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104-54-1

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104-54-1 Usage

Description

Different sources of media describe the Description of 104-54-1 differently. You can refer to the following data:
1. As an organic compound, Cinnamyl alcohol has a very distinct sweet, spicy, hyacinth odour that is found in resins, balsams and cinnamon leaves. It is used commonly in the fragrance industry due to its distinctive odour, which can be applied as a deodorant, fragrance and additive in cosmetic products and in the formulation of bath products, body and hand products, such as soaps, toothpaste, deodorants, etc. Besides, it also finds application as a food additive in chewing gum, bakery products, candy and soft drinks. Naturally, Cinnamyl alcohol is occurrent only in small amount, thus its industrial demand is usually fulfilled by chemical synthesis starting from the reduction of cinnamaldehyde. Cinnamyl alcohol has been found to have a sensitising effect on some particular people, thus it is also considered as a Standardized Chemical Allergen. The physiologic effect of cinnamyl alcohol is caused by the Increased Histamine Release and cell-mediated Immunity.
2. Occupational cases of contact dermatitis were reported in the perfurne industry. Patch tests can also be positive in food handlers. Cinnamic alcohol is contained in the "fragrance mix".

Uses

Different sources of media describe the Uses of 104-54-1 differently. You can refer to the following data:
1. Cinnamyl alcohol is valuable in perfumery for its odor and fixative properties. It is a component of many flower compositions (lilac, hyacinth, and lily of the valley) and is a starting material for cinnamyl esters, several of which are valuable fragrance materials. In flavor compositions, the alcohol is used for cinnamon notes and for rounding off fruit aromas.
2. Cinnamic alcohol is a component in perfumed cosmetic products and deodorants; some perfumery uses (cinnamon; daffodil; hyacinth; jasmine); natural occurrence (cinnamon).
3. Cinnamyl alcohol was used to study the alkylation of 2,4-di-tert-butylphenol by cinnamyl alcohol using aluminum-containing mesoporous ethane-silica catalyst. It was used to study gold nanoparticles supported on titanium dioxide catalysed oxidative coupling of alcohols and amines to form the corresponding imines.
4. cinnamyl alcohol is naturally occurring in cinnamon bark, it can also be synthetically manufactured. It is used in cosmetics as a fragrance or flavoring agent.In perfumery; as deodorant in 12.5% solution in glycerol.

Preparation

Different sources of media describe the Preparation of 104-54-1 differently. You can refer to the following data:
1. Cinnamyl alcohol is prepared on an industrial scale by reduction of cinnamaldehyde. Three methods are particularly useful: 1) In the Meerwein–Ponndorf reduction, cinnamaldehyde is reduced to cinnamic alcohol (yield about 85%) with isopropyl or benzyl alcohol in the presence of the corresponding aluminum alcoholate. 2) A 95% yield of Cinnamyl alcohol is obtained by selective hydrogenation of the carbonyl group in cinnamaldehydewith, for example, an osmium–carbon catalyst. 3) High yields of Cinnamyl alcohol can be obtained by reduction of cinnamaldehyde with alkali borohydrides. Formation of dihydrocinnamic alcohol is thus avoided.
2. By reduction of cinnamic aldehyde.

References

https://en.wikipedia.org/wiki/Cinnamyl_alcohol http://www.huidziekten.nl/allergie/stoffen/cinnamic-alcohol.htm https://www.ulprospector.com/en/na/Food/Detail/13286/411638/Cinnamic-Alcohol http://www.cosmeticsinfo.org/ingredient/cinnamyl-alcohol-0 https://pubchem.ncbi.nlm.nih.gov/compound/cinnamyl_alcohol#section=Top http://www.somaiya.com/products/chemicals-pipeline/cinnamic-alcohol-1

Chemical Properties

Different sources of media describe the Chemical Properties of 104-54-1 differently. You can refer to the following data:
1. Cinnamyl alcohol can exist in (Z)-[4510-34-3] and (E)-[4407-36-7] forms. Although both isomers occur in nature, the (E)-isomer is far more abundant and is present, for example, in styrax oil. (E)-Cinnamyl alcohol is a colorless, crystalline solid with a hyacinth-like balsamic odor. Cinnamyl alcohol can be dehydrogenated to give cinnamaldehyde and oxidized to give cinnamic acid. Hydrogenation yields 3-phenylpropanol and/or 3-cyclohexylpropanol. Reaction with carboxylic acids or carboxylic acid derivatives results in the formation of cinnamyl esters, some of which are used as fragrance materials.
2. Cinnamyl alcohol has a pleasant, floral odor and bitter taste.

Occurrence

Occurring as an ester or in the free state in hyacinth, Aristolochia clematis, Xanthorrhoea hastilis and in the essence of daffodil flowers. It is also reported found in guava fruit and peel, lemon peel oil, cassia leaf, Bourbon vanilla and cinnamon bark, leaf and root.

Definition

ChEBI: A primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C2C bond unspecified).

Aroma threshold values

Detection: 1 ppm; cis- form, 81 ppb; trans- form, 2.8 ppm

Taste threshold values

Taste characteristics at 20 ppm: green, floral, spicy and honey with a fermented yeasty nuance.

Synthesis Reference(s)

Chemistry Letters, 5, p. 581, 1976The Journal of Organic Chemistry, 59, p. 6378, 1994 DOI: 10.1021/jo00100a046Tetrahedron Letters, 34, p. 257, 1993 DOI: 10.1016/S0040-4039(00)60561-0

Flammability and Explosibility

Notclassified

Contact allergens

Cinnamyl alcohol occurs (in esterified form) in storax, Myroxylon pereirae, cinnamon leaves, and hyacinth oil. It is obtained by the alkaline hydrolysis of storax and prepared synthetically by reducing cinnamal diacetate with iron filings and acetic acid, and from cinnamaldehyde by Meerwein-Ponndorf reduction with aluminum isopropoxide. Cinnamyl alcohol is contained in the “fragrance mix.” As a fragrance allergen, it has to be mentioned by name in cosmetics within the EU. Occupational cases of contact dermatitis were reported in perfume industry. Patch tests can be positive in food handlers.

Synthesis

Obtained originally by saponification of extraction from storax; synthetically, by reduction of cinnamaldehyde with sodium or potassium hydroxide.

Purification Methods

Crystallise the alcohol from diethyl ether/pentane. [Beilstein 6 I 281.]

Check Digit Verification of cas no

The CAS Registry Mumber 104-54-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 4 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 104-54:
(5*1)+(4*0)+(3*4)+(2*5)+(1*4)=31
31 % 10 = 1
So 104-54-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+

104-54-1 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • TCI America

  • (C0362)  Cinnamyl Alcohol  >97.0%(GC)

  • 104-54-1

  • 25g

  • 100.00CNY

  • Detail
  • TCI America

  • (C0362)  Cinnamyl Alcohol  >97.0%(GC)

  • 104-54-1

  • 500g

  • 345.00CNY

  • Detail
  • Sigma-Aldrich

  • (93066)  Cinnamylalcohol  analytical standard

  • 104-54-1

  • 93066-50MG

  • 1,100.97CNY

  • Detail

104-54-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name cinnamyl alcohol

1.2 Other means of identification

Product number -
Other names 3-Phenyl

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:104-54-1 SDS

104-54-1Synthetic route

3-phenyl-propenal
104-55-2

3-phenyl-propenal

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With diphenylsilane; cesium fluoride at 25℃; for 0.05h;100%
With C28H28Cl2N4Pd; hydrogen In methanol at 30 - 35℃; under 760.051 Torr; for 8h; chemoselective reaction;100%
With C8H15BN2OS2; scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; Reagent/catalyst; Schlenk technique; Inert atmosphere;100%
3-phenyl-2-propenyl tetrahydro-2H-pyran-2-yl ether
99441-44-8, 80356-15-6

3-phenyl-2-propenyl tetrahydro-2H-pyran-2-yl ether

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
bis(trimethylsilyl)sulphate In methanol; 1,2-dichloro-ethane for 1h; Ambient temperature;100%
With methanol at 20℃; for 0.5h;98%
With lithium borohydride In methanol at 20℃; for 0.416667h;96%
trimethylsilyl cinnamyl ether
109283-53-6, 141427-94-3, 18042-41-6

trimethylsilyl cinnamyl ether

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With iodine In methanol microwave irradiation;100%
With bismuth(lll) trifluoromethanesulfonate In methanol at 20℃; for 0.0333333h;97%
With poly (ethylene glycol)-sulfonated sodium montmorillonite nanocomposite In methanol at 20℃; for 0.0833333h;96%
cinnamyl formate
104-65-4

cinnamyl formate

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With hydrogenchloride In acetone at 20℃; for 0.25h;100%
With ethanol; 1,3-bis(mesityl)imidazolium chloride In tetrahydrofuran at 45℃; for 1h;100%
1-(tert-butyldimethylsilyloxy)-3-phenyl-2-propene
71700-50-0

1-(tert-butyldimethylsilyloxy)-3-phenyl-2-propene

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With iodine In methanol microwave irradiation;100%
With hafnium tetrakis(trifluoromethanesulfonate) In methanol at 20℃; for 4h;96%
With bismuth(lll) trifluoromethanesulfonate In methanol at 20℃; for 0.333333h;90%
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
Stage #1: ethyl 3-phenyl-2-propenoate With C48H62ErN7O2Si2; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 110℃; for 6h; Inert atmosphere;
Stage #2: With silica gel In methanol at 60℃; for 3h; Inert atmosphere;
99%
With bis(acetylacetonato)dioxidomolybdenum(VI); 1,1,3,3-Tetramethyldisiloxane; Triphenylphosphine oxide In toluene at 100℃; for 72h; Inert atmosphere; Sealed tube;82%
With potassium borohydride; lithium chloride for 0.0833333h; microwave irradiation;55 % Chromat.
cinnamyl acetate
103-54-8

cinnamyl acetate

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With methanol at 80℃; for 6h; Inert atmosphere; Schlenk technique;99%
With methanol; potassium permanganate at 25℃; chemoselective reaction;94%
With 2C33H37N*H2O7S2; water at 40℃; for 24h;93%
methyl cinnamate
103-26-4

methyl cinnamate

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
Stage #1: methyl cinnamate With diethylzinc; lithium chloride In tetrahydrofuran; hexane at 20℃; for 6h; Inert atmosphere;
Stage #2: With sodium hydroxide In tetrahydrofuran; hexane; water at 20℃; for 8h; Inert atmosphere; chemoselective reaction;
98%
With Li(1+)*C12H28AlO3(1-) In tetrahydrofuran; hexane for 0.5h; Ambient temperature;97%
With sodium tetrahydroborate; ethanol; cerium(III) chloride heptahydrate at 20℃; for 24h; chemospecific reaction;95%
1-Phenyl-2-propen-1-ol
4393-06-0

1-Phenyl-2-propen-1-ol

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With triphenylsilyl perrhenate In diethyl ether at 0℃; for 0.5h;98%
With silica-supported monomeric vanadium-oxo species In acetonitrile at 20℃; for 6h; Reagent/catalyst; Temperature; Inert atmosphere;95%
With salicylic acid In water; acetonitrile for 16h; Reflux;90%
C15H20O2
1146218-82-7

C15H20O2

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
Stage #1: C15H20O2 With 2,4,6-trimethyl-pyridine; triethylsilyl trifluoromethyl sulfonate In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: With water In dichloromethane Inert atmosphere;
98%
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

A

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

B

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With hydrogen; (1,5-cyclooctadiene)(methoxy)iridium(l) dimer; ethyl-diphenyl-phosphane In toluene at 100℃; under 22800 Torr; for 7h; Product distribution; other catalysts, times, solvent;A 1%
B 97%
With hydrogen; (1,5-cyclooctadiene)(methoxy)iridium(l) dimer In toluene at 100℃; under 22800 Torr; for 7h;A 1%
B 97%
With C48H43ClN2P2Ru; potassium carbonate; isopropyl alcohol In neat (no solvent) at 90℃; for 1h; Catalytic behavior; Reagent/catalyst; Concentration; Schlenk technique;A 7 %Spectr.
B 90 %Spectr.
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With C48H43ClN2P2Ru; ammonium formate In water; toluene at 90℃; for 10h; Catalytic behavior; Schlenk technique;97%
With n-butyllithium In diethyl ether; hexane at -78 - 20℃; Inert atmosphere;89%
With hydrogen In acetonitrile at 90℃; under 22502.3 Torr; for 2h; Reagent/catalyst; Flow reactor;32.4%
cinnamyl chloride
2687-12-9

cinnamyl chloride

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With iron(III) sulfate; water In toluene at 110℃; for 1h; Ionic liquid;96%
iodobenzene
591-50-4

iodobenzene

allyl alcohol
107-18-6

allyl alcohol

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With Pd(0) nanoparticles immobilized in TpPa-1 at 105℃; for 6h; Catalytic behavior; Heck Reaction;95%
With potassium carbonate In water at 100℃; for 12h; Catalytic behavior; Temperature; Time; Heck Reaction; Green chemistry;30 %Chromat.
methanol
67-56-1

methanol

Cinnamic acid
621-82-9

Cinnamic acid

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With tert.-butylhydroperoxide In water at 110℃; for 4h; Sealed tube;94%
Cinnamoyl chloride
102-92-1

Cinnamoyl chloride

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With poly-η-(pyridine)zinc borohydride In diethyl ether for 3.5h; Ambient temperature;93%
Cinnamic acid
621-82-9

Cinnamic acid

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
Stage #1: Cinnamic acid With 4-methyl-morpholine; 1,3,5-trichloro-2,4,6-triazine In 1,2-dimethoxyethane at 20℃; for 3h; Esterification;
Stage #2: With sodium tetrahydroborate In water at 0℃; Reduction;
93%
Stage #1: Cinnamic acid With sodium aminodiboranate In tetrahydrofuran at 20℃;
Stage #2: With water Solvent;
90%
With tributylphosphine; diphenylsilane; C45H25F12N7Ni2O9 In 1,4-dioxane at 100℃; for 16h;80%
2-(cinnamyloxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(cinnamyloxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With silica gel In ethyl acetate; Petroleum ether93%
In methanol at 20℃; for 5h; Inert atmosphere; Glovebox;86%
With silica gel at 25℃; Inert atmosphere; Glovebox;78%
C22H22OSi

C22H22OSi

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With Nonafluorobutanesulfonyl fluoride; TPGS-750-M In propan-1-ol; water at 50℃; for 8h; Reagent/catalyst; Solvent; Temperature; Green chemistry; chemoselective reaction;93%
3-phenyl-propenal
104-55-2

3-phenyl-propenal

A

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

B

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; antimony(III) chloride In tetrahydrofuran at 0℃; for 4h;A 7%
B 92%
With [Ru(2-(methylthio)-N-[(pyridin-2-yl)methyl]ethan-1-amine)(triphenylphosphine)Cl2]; potassium tert-butylate; hydrogen In isopropyl alcohol at 80℃; under 22502.3 Torr; for 16h; Reagent/catalyst; Inert atmosphere;A 5%
B 84%
With hydrogen In 1,4-dioxane at 180℃; under 7500.75 Torr; for 18h; Reagent/catalyst; Autoclave;A n/a
B 76%
3-Phenyl-2-propyn-1-ol
1504-58-1

3-Phenyl-2-propyn-1-ol

A

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

B

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With hydrogen; poly(amidoamine) dendron-stabilised Pd(0) nanoparticle In dichloromethane at 25℃; under 760.051 Torr; for 3h;A 8%
B 92%
With 1,1'-bis(diphenylphosphino)ferrocene; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; Butane-1,4-diol; potassium tert-butylate at 110℃; for 24h; Inert atmosphere;
C30H28O3

C30H28O3

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With cerium(III) chloride; sodium iodide In acetonitrile for 5h; ether cleavage; Heating;90%
diisopropyl-1H,1H,2H,2H-perfluorodecylsilyl cinnamyl ether
374928-86-6

diisopropyl-1H,1H,2H,2H-perfluorodecylsilyl cinnamyl ether

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With fluorosilicic acid In methanol; acetonitrile for 36h;90%
C16H16O2

C16H16O2

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone Product distribution / selectivity;90%
C12H16O2
1146218-83-8

C12H16O2

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
Stage #1: C12H16O2 With 2,4,6-trimethyl-pyridine; triethylsilyl trifluoromethyl sulfonate In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: With water In dichloromethane Inert atmosphere; chemoselective reaction;
90%
trans (3-phenyloxiran-2-yl)methanol

trans (3-phenyloxiran-2-yl)methanol

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With carbon monoxide In water at 27℃; under 760.051 Torr; for 16h; chemoselective reaction;90%
Conditions
ConditionsYield
With carbon monoxide; water at 27℃; under 760.051 Torr; for 16h; chemoselective reaction;A 90%
B n/a
1-(4-methoxybenzyloxy)-3-phenylprop-2-ene
282716-03-4

1-(4-methoxybenzyloxy)-3-phenylprop-2-ene

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With trichlorophosphate In 1,2-dichloro-ethane at 20℃; for 0.833333h;90%
With silver hexafluoroantimonate; 1,2,3-trimethoxybenzene In dichloromethane at 40℃; for 2h;2%
(E)-1-tert-butyldimethylsilyloxy-3-phenyl-2-propene
100009-29-8

(E)-1-tert-butyldimethylsilyloxy-3-phenyl-2-propene

CsCO3

CsCO3

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 100℃; for 3h;89%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

Conditions
ConditionsYield
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 2h; chemoselective reaction;100%
With hydrogen In water at 20℃; under 760.051 Torr; for 2h; Sealed tube;100%
With hydrogen In ethanol at 100℃; under 30003 Torr; Flow reactor; Green chemistry; chemoselective reaction;100%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

Cinnamyl bromide
4392-24-9

Cinnamyl bromide

Conditions
ConditionsYield
With 1,1,1,2,2,2-hexamethyldisilane; pyridinium hydrobromide perbromide In chloroform at 25℃; for 0.5h;100%
With chloro-trimethyl-silane; lithium bromide In acetonitrile for 12h; Heating;93%
With carbon tetrabromide; polystyrene-supported triphenylphosphine In chloroform at 20℃; for 0.166667h;89%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With dimethyl selenoxide In dichloromethane for 7h; Heating;100%
With 2,2'-bipyridylchromium peroxide In benzene for 1.25h; Heating;100%
With tert.-butylhydroperoxide; polystyrene-bound phenylselenic acid In tetrachloromethane for 63h; Heating;100%
Dimethoxymethane
109-87-5

Dimethoxymethane

3-Phenylpropenol
104-54-1

3-Phenylpropenol

γ-Phenyl-allylalkohol-methoxy-methylether
88738-40-3, 91970-13-7

γ-Phenyl-allylalkohol-methoxy-methylether

Conditions
ConditionsYield
With toluene-4-sulfonic acid; lithium bromide for 0.75h; Ambient temperature;100%
With 12-tungstophosphoric acid immobilized on [bmim][FeCl4] at 75 - 82℃; for 0.00555556h; Microwave irradiation;98%
With 1-butyl-3-methylimidazolium tetrachloroindate for 0.025h; Microwave irradiation; chemoselective reaction;97%
With tin(IV)octabromotetraphenylporphyrinato trifluoromethanesulfonate at 20℃; for 0.0833333h;95%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

Conditions
ConditionsYield
With Ir(ClO4)(CO)(PPh3)2; hydrogen In chloroform-d1 at 25℃; under 760 Torr; for 3h;100%
With (1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; hydrogen In tetrahydrofuran at 23℃; for 1h;100%
With 20 % Pd(OH)2/C; hydrogen In benzene at 20℃; Inert atmosphere;92%
benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

3-Phenylpropenol
104-54-1

3-Phenylpropenol

A

methanol
67-56-1

methanol

B

cinnamyl benzoate
5320-75-2

cinnamyl benzoate

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 100%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

benzoic acid ethyl ester
93-89-0

benzoic acid ethyl ester

A

ethanol
64-17-5

ethanol

B

cinnamyl benzoate
5320-75-2

cinnamyl benzoate

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 100%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

3-phenylpropanoic acid methyl ester
103-25-3

3-phenylpropanoic acid methyl ester

A

methanol
67-56-1

methanol

B

3-phenyl-2-propenyl benzenepropanoate
140671-25-6, 28048-98-8

3-phenyl-2-propenyl benzenepropanoate

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 100%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

A

ethanol
64-17-5

ethanol

B

3-phenyl-2-propenyl benzenepropanoate
140671-25-6, 28048-98-8

3-phenyl-2-propenyl benzenepropanoate

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 100%
benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

3-Phenylpropenol
104-54-1

3-Phenylpropenol

cinnamyl benzoate
5320-75-2

cinnamyl benzoate

Conditions
ConditionsYield
[Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In various solvent(s) at 150℃; for 16h;100%
With iron(III)-acetylacetonate In n-heptane at 105℃; for 20h; Inert atmosphere;96%
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

3-Phenylpropenol
104-54-1

3-Phenylpropenol

3-phenyl-2-propen-1-yl 3-phenylacrylate
40918-97-6, 61019-10-1, 122-69-0

3-phenyl-2-propen-1-yl 3-phenylacrylate

Conditions
ConditionsYield
[Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In toluene at 150℃; for 16h;100%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

benzoic acid ethyl ester
93-89-0

benzoic acid ethyl ester

cinnamyl benzoate
5320-75-2

cinnamyl benzoate

Conditions
ConditionsYield
[Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In various solvent(s) at 150℃; for 16h;100%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

3-phenylpropanoic acid methyl ester
103-25-3

3-phenylpropanoic acid methyl ester

3-phenyl-2-propenyl benzenepropanoate
140671-25-6, 28048-98-8

3-phenyl-2-propenyl benzenepropanoate

Conditions
ConditionsYield
[Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In various solvent(s) at 150℃; for 16h;100%
With zinc diacetate In toluene for 18h; Reflux;
3-Phenylpropenol
104-54-1

3-Phenylpropenol

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

3-phenyl-2-propenyl benzenepropanoate
140671-25-6, 28048-98-8

3-phenyl-2-propenyl benzenepropanoate

Conditions
ConditionsYield
[Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In various solvent(s) at 150℃; for 16h;100%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

bis-cinnamyl-phosphinic acid

bis-cinnamyl-phosphinic acid

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); hypophosphorous acid; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tert-Amyl alcohol at 102℃; for 24h; Molecular sieve; Inert atmosphere;100%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

phenylphosphinic acid
1779-48-2

phenylphosphinic acid

cinnamyl(phenyl)phosphonic acid

cinnamyl(phenyl)phosphonic acid

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tert-Amyl alcohol at 102℃; for 24h; Inert atmosphere;100%
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,2-dimethoxyethane; N,N-dimethyl-formamide at 115℃; for 24h;87%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

N-phenyl-benzimidoyl chloride
4903-36-0

N-phenyl-benzimidoyl chloride

3-phenylallyl (N-phenyl)benzimidate

3-phenylallyl (N-phenyl)benzimidate

Conditions
ConditionsYield
Stage #1: 3-Phenylpropenol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 30℃; for 1.25h;
Stage #2: N-phenyl-benzimidoyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; for 20h;
100%
Stage #1: 3-Phenylpropenol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 2h;
Stage #2: N-phenyl-benzimidoyl chloride In tetrahydrofuran; mineral oil for 2h;
Stage #3: With tert-butyl methyl ether In tetrahydrofuran; water; mineral oil
2-bromoisobutyric acid bromide
20769-85-1

2-bromoisobutyric acid bromide

3-Phenylpropenol
104-54-1

3-Phenylpropenol

cinnamyl 2-bromo-2-methylpropanoate
60533-00-8

cinnamyl 2-bromo-2-methylpropanoate

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 0℃; for 1.5h; Inert atmosphere;100%
Stage #1: 3-Phenylpropenol With sodium hydride In dichloromethane; mineral oil at 20℃; for 0.166667h;
Stage #2: 2-bromoisobutyric acid bromide In dichloromethane; mineral oil at 20℃;
3-Phenylpropenol
104-54-1

3-Phenylpropenol

anthranilic acid
118-92-3

anthranilic acid

2-(cinnamylamino)benzoic acid
99753-82-9

2-(cinnamylamino)benzoic acid

Conditions
ConditionsYield
With palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 70℃; stereoselective reaction;100%
diiodomethane
75-11-6

diiodomethane

3-Phenylpropenol
104-54-1

3-Phenylpropenol

(trans)-(2-phenylcyclopropyl)methanol

(trans)-(2-phenylcyclopropyl)methanol

Conditions
ConditionsYield
With diethylzinc In hexane; dichloromethane at 0 - 20℃; for 18.5h;100%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

butyl cinnamyl-H-phosphinate
1012339-08-0

butyl cinnamyl-H-phosphinate

butyl bis cinnamylphosphinate

butyl bis cinnamylphosphinate

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tert-Amyl alcohol for 24h; Reflux; Inert atmosphere; Dean-Stark;100%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

butyl (2-ethylphthalimide)-H-phosphinate

butyl (2-ethylphthalimide)-H-phosphinate

butyl (2-ethylphthalimide)cinnamylphosphinate

butyl (2-ethylphthalimide)cinnamylphosphinate

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tert-Amyl alcohol for 24h; Reflux; Inert atmosphere; Dean-Stark;100%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

acetic anhydride
108-24-7

acetic anhydride

cinnamyl acetate
103-54-8

cinnamyl acetate

Conditions
ConditionsYield
With Cp2Ti(OSO2C8F17)2 at 20℃; for 0.0833333h; Neat (no solvent);99%
With pyridine In dichloromethane at 20℃; for 24h; Inert atmosphere;99%
cerium triflate In acetonitrile at 20℃; for 2.5h;98%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

benzoyl chloride
98-88-4

benzoyl chloride

cinnamyl benzoate
5320-75-2

cinnamyl benzoate

Conditions
ConditionsYield
Stage #1: 3-Phenylpropenol With dmap; triethylamine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: benzoyl chloride In dichloromethane for 15h; Inert atmosphere;
99%
Stage #1: 3-Phenylpropenol With pyridine; dmap In dichloromethane at 5℃; for 0.166667h; Inert atmosphere; Sealed tube;
Stage #2: benzoyl chloride In dichloromethane at 5 - 20℃; for 16h; Inert atmosphere; Sealed tube;
89%
With samarium In acetonitrile at 70℃; for 0.05h;77%
trimethylsilylazide
4648-54-8

trimethylsilylazide

3-Phenylpropenol
104-54-1

3-Phenylpropenol

trimethylsilyl cinnamyl ether
109283-53-6, 141427-94-3, 18042-41-6

trimethylsilyl cinnamyl ether

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h; Ambient temperature;99%

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104-54-1Relevant articles and documents

Catalytic hydrosilylation of carbonyl compounds by hydrido thiophenolato iron(II) complexes

Xue, Benjing,Sun, Hongjian,Niu, Qingfen,Li, Xiaoyan,Fuhr, Olaf,Fenske, Dieter

, p. 23 - 28 (2017)

The hydrosilylation of aldehydes and ketones under mild conditions with hydrido thiophenolato iron(II) complexes [cis–Fe(H)(SAr)(PMe3)4] (1–4) as catalysts is reported using (EtO)3SiH as an efficient reducing agent in the yields up to 95%. Among them complex 1 is the best catalyst. Complex 1 could also be used as catalyst to reduce the α,β-unsaturated carbonyl compounds selectively to the α,β-unsaturated alcohols in high yields.

Zn(BH4)2/ultrasonic irradiation: An efficient system for reduction of carbonyl compounds to their corresponding alcohols

Fanari, Siamak,Setamdideh, Davood

, p. 695 - 697 (2014)

Zn(BH4)2 under ultrasonic irradiation is an efficient reducing system in CH3CN. This system reduces a variety of carbonyl compounds to their corresponding alcohols at room temperature in high to excellent yields of the products. Also, a,b-unsaturated aldehydes and ketones was regioselectively reduced to the corresponding allylic alcohols.

Conversion of alkyl halides into the corresponding alcohols under mild reaction conditions

Ruddick, Clare L.,Hodge, Philip,Houghton, Mark P.

, p. 1359 - 1362 (1996)

Reaction of primary, cyclopentyl, allyl and arylmethyl halides, but not an acyclic secondary halide or a tertiary halide, in acetone or tetrahydrofuran with the formate form of a commercial anion exchange resin gave formate esters in good yields. The formates were hydrolysed efficiently to the corresponding alcohols by a brief treatment with hydrochloric acid. Reaction of primary alkyl bromides or iodides, secondary alkyl bromides, cinnamyl and arylmethyl halides in tetrahydropyran or 1,4-dioxane with the bicarbonate form of the same anion-exchange resin gave the corresponding alcohols directly in good yields. This latter reaction can be carried out successfully in the presence of ester or amide groups.

Exclusive 1,2-reduction of functionalised conjugated aldehydes with sodium triacetoxyborohydride

Singh, Jasvinder,Sharma, Munisha,Kaur, Irvinder,Kad, Goverdhan L.

, p. 1515 - 1519 (2000)

Functionalised α,β-unsaturated aldehydes were exclusively reduced to allylic alcohols with sodium-triacetoxyborohydride. Neither saturated alcohol nor saturated aldehydes are obtained. Conjugated ketones are not reduced.

Core-shell AgNP@CeO2 nanocomposite catalyst for highly chemoselective reductions of unsaturated aldehydes

Mitsudome, Takato,Matoba, Motoshi,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi

, p. 5255 - 5258 (2013)

Selective silver: A core-shell AgNP-CeO2 nanocomposite (AgNP@CeO2) acted as an effective catalyst for the chemoselective reductions of unsaturated aldehydes to unsaturated alcohols with H2 (see figure). Maximizing the AgNP-CeO2 interaction successfully induced the heterolytic cleavage of H2, resulting in highly chemoselective reductions. Furthermore, a highly dispersed AgNP@CeO2 system was also developed that exhibited a higher activity than the original AgNP@CeO2. Copyright

Pinacol coupling of aromatic aldehydes and ketones using TiCl 3-Al-EtOH under ultrasound irradiation

Li, Ji-Tai,Lin, Zhi-Ping,Qi, Na,Li, Tong-Shuang

, p. 4339 - 4348 (2004)

Titanium trichloride in EtOH can be reduced by Al to the corresponding low-valent titanium complexes. This can reduce some aromatic aldehydes and ketones to the corresponding pinacols in 40-82% yields within 30-90 min at r.t. under ultrasound irradiation.

A SIMPLE PROCEDURE FOR THE SYNTHESIS OF THREE-CARBON HOMOLOGATED BORONATE ESTERS AND TERMINAL ALKENES VIA NUCLEOPHILIC DISPLACEMENT IN α-HALOALLYLBORONATE ESTER

Brown, Herbert C.,Rangaishenvi, Milind V.

, p. 7115 - 7118 (1990)

The transfer reactions of α-haloallylboronate ester 1 with representative organolithium and Grignard reagents provide α-alkyl- or α-aryl-substituted allylboronate esters, readily converted into three-carbon homologated boronate esters and terminal alkenes.

Cofactor recycling for selective enzymatic biotransformation of cinnamaldehyde to cinnamyl alcohol

Zucca, Paolo,Littarru, Maria,Rescigno, Antonio,Sanjust, Enrico

, p. 1224 - 1226 (2009)

The enzymatic, selective hydrogenation of cinnamaldehyde to cinnamyl alcohol is reported here. Yeast alcohol dehydrogenase was used in a substrate-coupled process with cofactor recycling. Both 100% selectivity and aldehyde conversion were achieved within

Poly(1,4-butyl-bis-vinylpyridinium) borohydride as a new stable and efficient reducing agent in organic synthesis

Khaligh, Nader Ghaffari

, p. 721 - 727 (2013)

The unstable sodium borohydride is stabilized on modified poly(4-vinylpyridinium), and it is used as an efficient and regenerable polymer-supported borohydride reagent for the reduction of a variety of carbonyl compounds, such as aldehydes, ketones, α,β-unsaturated carbonyl compounds, α-diketones and acyloins, in good to excellent yields.

Quaternized amino functionalized cross-linked polyacrylamide as a new solid - Liquid phase transfer catalyst in reduction of carbonyl compounds with NaBH4

Tamami, Bahman,Mahdavi, Hossein

, p. 821 - 826 (2003)

Poly[N-(2-aminoethyl)acrylamido]trimethyl ammonium chloride resin was developed as a new polymeric phase transfer catalyst. This quaternized polyacrylamide catalyzed the chemoselective reduction of aldehydes and ketones by NaBH4 to give corresponding alcohols in high yields under mild conditions.

Promotion of Sn on the Pd/AC catalyst for the selective hydrogenation of cinnamaldehyde

Zhao, Jia,Xu, Xiaoliang,Li, Xiaonian,Wang, Jianguo

, p. 102 - 106 (2014)

The effect of Sn on the Pd/AC catalysts for the selective hydrogenation of cinnamaldehyde (CALD) was investigated. TEM, EDX, XRD and XPS have been employed to characterize Pd-Sn/AC. 80% cinnamyl alcohol (COL) selectivity can be obtained at 96% CALD conversion, even 100% selectivity can be achieved at 3% conversion. The PdSn type alloy is responsible for the enhancement of unsaturated alcohol (UA) selectivity, as confirmed by XRD and EDX. XPS technique confirmed that the promoting effect of Sn was related to Pd-Sn interaction. The favorable adsorption of C = O bond on the PdSn has been supported by means of density functional theory.

Cationic [2,6-Bis(2′-oxazolinyl)phenyl]palladium(II) Complexes: Catalysts for the Asymmetric Michael Reaction

Stark, Mark A.,Jones, Geraint,Richards, Christopher J.

, p. 1282 - 1291 (2000)

Reaction of 1,3-dicyanobenzene with β-amino alcohols (S)-H2NCHRCH2OH (R = iPr, iBu, tBu, CH2Cy, CH2Ph) and (R)-H2NCHPhCH2OH gave new 1,3-bis(2′-oxazolinyl)benzenes (30-51%). These, together with 1,3-bis(4′,4′-dimethyl-2′-oxazolinyl)benzene, were treated with LDA/TMEDA followed by the addition of PdBr2(1,5-COD) to give [2,6-bis(2′-oxazolinyl)phenyl]-palladium(II) bromide complexes (21-41%). In two cases no complexes were obtained (R = Ph, CH2Ph) due to ring opening of the oxazolines by LDA/TMEDA. Treatment of the palladium complexes with AgBF4, AgOTf, or AgSbF6 in wet CH2Cl2 provided a series of cationic [2,6-bis(2′-oxazolinyl)phenyl]palladium complexes (28-87%) containing water coordinated to palladium, as established by an X-ray crystal structure analysis of (S,S)-[2,6-bis(4′-isopropyl-2′-oxazolinyl)phenyl]aquopalladium(II) trifluoromethanesulfonate. All of the cationic complexes proved to be efficient catalysts for the Michael reaction between α-cyanocarboxylates and methyl vinyl ketone and between acrylonitrile and activated Michael donors. Selectivities of up to 34% ee were obtained for the formation of (R)-ethyl 2-cyano-2-methyl-5-oxohexanoate.

Pyridine: N-oxide promoted hydrosilylation of carbonyl compounds catalyzed by [PSiP]-pincer iron hydrides

Chang, Guoliang,Fenske, Dieter,Fuhr, Olaf,Li, Xiaoyan,Sun, Hongjian,Xie, Shangqing,Yang, Wenjing,Zhang, Peng

, p. 9349 - 9354 (2020)

Five [PSiP]-pincer iron hydrides 1-5, [(2-Ph2PC6H4)2HSiFe(H)(PMe3)2 (1), (2-Ph2PC6H4)2MeSiFe(H)(PMe3)2 (2), (2-Ph2PC6H4)2PhSiFe(H)(PMe3)2 (3), (2-(iPr)2PC6H4)2HSiFe(H)(PMe3) (4), and (2-(iPr)2PC6H4)2MeSiFe(H)(PMe3)2 (5)], were used as catalysts to study the effects of pyridine N-oxide and the electronic properties of [PSiP]-ligands on the catalytic hydrosilylation of carbonyl compounds. It was proved for the first time that this catalytic process could be promoted with pyridine N-oxide as the initiator at 30 °C because the addition of pyridine N-oxide is beneficial for the formation of an unsaturated hydrido iron complex, which is the key intermediate in the catalytic mechanism. Complex 4 as the best catalyst shows excellent catalytic performance. Among the five complexes, complex 3 was new and the molecular structure of complex 3 was determined by single crystal X-ray diffraction. A proposed mechanism was discussed.

Hydrogenation of α,β-Unsaturated Aldehydes and Ketones to the Unsaturated Alcohols catalysed by Hydridoiridium Phosphine Complexes

Farnetti, E.,Pesce, M.,Kaspar, J.,Spogliarich, R.,Graziani, M.

, p. 746 - 747 (1986)

Unusual selective hydrogenation of cinnamaldehyde and benzylideneacetone to the corresponding unsaturated alcohols is catalysed by (+) complexes in toluene; use of a chiral phosphine gives a 7.4percent enantiomeric excess of (S)-(-)-1-phenylbut-1-en-3-ol.

Iron-Catalyzed Allylic Amination Directly from Allylic Alcohols

Emayavaramban, Balakumar,Roy, Moumita,Sundararaju, Basker

, p. 3952 - 3955 (2016)

Allylic amination, directly from alcohols, has been demonstrated without any Lewis acid activators using an efficient and regiospecific molecular iron catalyst. Various amines and alcohols were employed and the reaction proceeded through the oxidation/reduction (redox) pathway. A direct one-step synthesis of common drugs, such as cinnarizine and nafetifine, was exhibited from cinnamyl alcohol that produced water as side product. The iron way! A direct amination of allylic alcohols has been demonstrated without the need of Lewis acid activators using an efficient and regiospecific molecular iron catalyst. A range of amines and alcohols were tolerated, and the reaction was found to procced through an oxidation/reduction (redox) pathway (see scheme).

Polymer Supported Zirconium Borohydride: a Stable, Efficient and Regenerable Reducing Agent

Tamami, Bahman,Goudarzian, Nouredin

, p. 1079 - 1080 (1994)

The unstable zirconium borohydride, Zr(BH4)4, is stabilized on polyvinylpyridine and used as a new, stable, efficient and regenerable polymer supported transition-metal borohydride reagent for reduction of a variety of carbonyl compounds.

Chemoselective transfer hydrogenation of carbonyl compounds catalyzed by macrocyclic nickel (II)complex

Phukan, Prodeep,Sudalai

, p. 2401 - 2405 (2000)

Macrocyclic Ni(II) complex, 1, catalyzes efficiently the chemoselective transfer reduction of carbonyl compounds in presence of propan-2-ol/KOH or HCO2H/HCO2NH4 as hydrogen donors to produce the corresponding alcohols in high yield.

Hydrosilylation of aldehydes and ketones catalyzed by an n-heterocyclic carbene-nickel hydride complex under mild onditions

Bheeter, Linus P.,Henrion, Mickael,Brelot, Lydia,Darcel, Christophe,Chetcuti, Michael J.,Sortais, Jean-Baptiste,Ritleng, Vincent

, p. 2619 - 2624 (2012)

Half-sandwich N-heterocyclic carbene (NHC)-nickel complexes of the general formula [NiACHTUNGTRENUNG(NHC)ClCp?] (Cp?= Cp, Cp*) efficiently catalyze the hydrosilylation of aldehydes and ketones at room temperature in the presence of a catalytic amount of sodium triethylborohydride and thus join the fairly exclusive club of well-defined nickel(II) catalyst precursors for the hydrosilylation of carbonyl functionalities. Of notable interest is the isolation of an intermediate nickel hydride complex that proved to be the real catalyst precursor.

A mild and chemoselective method for the deprotection of tert-butyldimethylsilyl (TBDMS) ethers using iron(III) tosylate as a catalyst

Bothwell, Jason M.,Angeles, Veronica V.,Carolan, James P.,Olson, Margaret E.,Mohan, Ram S.

, p. 1056 - 1058 (2010)

The most common method for the deprotection of TBDMS ethers utilizes stoichiometric amounts of tetrabutylammonium fluoride, n-Bu4N+F- (TBAF), which is highly corrosive and toxic. We have developed a mild and chemoselective method for the deprotection of TBDMS, TES, and TIPS ethers using iron(III) tosylate as a catalyst. Phenolic TBDMS ethers, TBDPS ethers and the BOC group are not affected under these conditions. Iron(III) tosylate is an inexpensive, commercially available, and non-corrosive reagent.

SELECTIVE REDUCTION OF ALDEHYDES BY A FORMIC ACID- TRIALKYLAMINE- RuCl2(PPh3)3 SYSTEM

Khai, Bui The,Arcelli, Antonio

, p. 3365 - 3368 (1985)

In the presence of trialkylamine and formic acid, RuCl2(PPh3)3 selectively reduces aldehydes to the corresponding alkohols at room temperature.Other reducible groups are unaffected.

A mild method for the deprotection of tetrahydropyranyl (THP) ethers catalyzed by iron(III) tosylate

Bockman, Matthew R.,Angeles, Veronica V.,Martino, Julia M.,Vagadia, Purav P.,Mohan, Ram S.

, p. 6939 - 6941 (2011)

A mild method for the deprotection of THP ethers catalyzed by iron(III) tosylate (2.0 mol %) in CH3OH has been developed. Iron(III) tosylate, Fe(OTs)3·6H2O, is a commercially available solid that is inexpensive, noncorrosive, and easy to handle. The room temperature reaction conditions make this method attractive for deprotection of a range of THP ethers.

Caro's acid supported on silica gel. Part V: A mild and selective reagent for conversion of trimethyl silyl ethers to the corresponding hydroxy compounds

Lakouraj,Tajbakhsh,Khojasteh

, p. 1865 - 1870 (2003)

Mild and efficient method for deprotection of silyl ethers to alcohols is described using Caro's acid supported on silica gel. Reactions are carried out in dichloromethane at room temperature and their parent hydroxy compounds obtained in good to excellent yields. Using this procedure, tetrahydropyranyl ethers (THP) remain intact during desilylation reaction.

New heterogeneous B(OEt)3-MCM-41 catalyst for preparation of α,β-unsaturated alcohols

Uysal, Burcu,Oksal, Birsen S.

, p. 3893 - 3911 (2013)

Grafting of boron tri-ethoxide on mesoporous MCM-41 resulted in a highly active catalyst for the Meerwein-Ponndorf-Verley (MPV) reduction and the catalyst denoted as B(OEt)3-MCM-41. Chemoselective reduction of α,β-unsaturated aldehydes and ketones to the corresponding α,β-unsaturated alcohols was achieved by MPV reduction reaction using a new B(OEt)3-MCM-41 catalyst. The prepared new heterogeneous catalyst, B(OEt)3-MCM-41, was characterized in detail by using XRD, 29Si NMR-, 11B NMR-, 13C NMR-, and TEM, N2 adsorption, and ICP-OES. The results demonstrated the successful homogenous distribution of the B(OEt)3 on the MCM-41 support. The heterogeneous B(OEt)3-MCM-41 catalyst, in comparison with the homogeneous B(O i Pr)3 and B(OEt)3 catalysts, displayed similiar catalytic activity in the MPV reduction of α,β-unsaturated aldehydes and ketones with alcohols as reductants. Reduced reaction times and very high selectivities for the unsaturated alcohols were obtained with the heterogenous catalyst compared with the homogeneous catalysts. The B(OEt)3-MCM-41 catalyst was found to be encouraging, as is is recyclable up to six cycles without any significant loss in its catalytic activity.

-

Rylander,Steele

, p. 1579 (1969)

-

Chemoselective reduction of carbonyl compounds to alcohols with co-doped ammonia borane

Huang, Pengmian,Tang, Wenjuan,Tan, Guishan,Zeng, Wenbin,Li, Yuanjian,Zhang, Qinghua,Chen

, p. 8248 - 8250 (2014)

Chemoselective reduction of various carbonyl compounds to alcohols with Co-doped ammonia borane was investigated in the present work. It was observed that Co-doped ammonia borane exhibited much better performance than ammonia borane. The Co-based catalysts could be reused up to four times with a slight decrease in activity. Thus, a mild and efficient method for chemoselective reduction of carbonyl compounds with Co-doped ammonia borane was established. The Co-doped ammonia borane sample was characterized by electron paramagnetic resonance. Electron paramagnetic resonance characterization revealed that Co element in a partially reduced state.

Low-temperature reduction of bio-based cinnamaldehyde to α,β-(un)saturated alcohols enabled by a waste-derived catalyst

Jian, Yumei,Li, Hu,Luo, Xiaoxiang

, (2022/01/06)

A waste eggshell-derived catalyst (CaO-900) was facilely prepared and exhibited high efficiency in selective hydrogenation of bio-based cinnamaldehyde (CAL) to cinnamyl alcohol (COL) with 97% yield at 30 °C. By simply adjusting reaction temperature and time, CAL could be completely converted to 3-phenylpropanol. The predominant catalytic performance of CaO-900 could be attributed to its high alkalinity and large specific surface area. In situ Raman and theoretical calculations indicated that the priority of hydrosilylation toward CAL played a crucial role in the control of product distribution. In addition, the CaO-900 catalyst showed good recyclability.

Hydroboration Reaction and Mechanism of Carboxylic Acids using NaNH2(BH3)2, a Hydroboration Reagent with Reducing Capability between NaBH4and LiAlH4

Wang, Jin,Ju, Ming-Yue,Wang, Xinghua,Ma, Yan-Na,Wei, Donghui,Chen, Xuenian

, p. 5305 - 5316 (2021/04/12)

Hydroboration reactions of carboxylic acids using sodium aminodiboranate (NaNH2[BH3]2, NaADBH) to form primary alcohols were systematically investigated, and the reduction mechanism was elucidated experimentally and computationally. The transfer of hydride ions from B atoms to C atoms, the key step in the mechanism, was theoretically illustrated and supported by experimental results. The intermediates of NH2B2H5, PhCH= CHCOOBH2NH2BH3-, PhCH= CHCH2OBO, and the byproducts of BH4-, NH2BH2, and NH2BH3- were identified and characterized by 11B and 1H NMR. The reducing capacity of NaADBH was found between that of NaBH4 and LiAlH4. We have thus found that NaADBH is a promising reducing agent for hydroboration because of its stability and easy handling. These reactions exhibit excellent yields and good selectivity, therefore providing alternative synthetic approaches for the conversion of carboxylic acids to primary alcohols with a wide range of functional group tolerance.

Synthesis method of 2-benzoxepin compound

-

, (2021/05/29)

The invention discloses a synthesis method of a 2-benzoxepin compound. The method comprises the following specific steps: under the protection of nitrogen, adding N-phenylseleno-phthalimide into a reactor, then adding anhydrous dichloromethane to dissolve the N-phenylseleno-phthalimide, then adding a 1-[(cinnamyl) methyl]-3, 4, 5-trimethoxybenzene compound, taking zinc chloride as a catalyst, reacting at room temperature, adding saturated sodium bicarbonate for quenching after the reaction is finished, extracting by dichloromethane, combining organic phases, drying by anhydrous magnesium sulfate, concentrating under reduced pressure, and performing silica gel rapid chromatographic purification by thin-layer chromatography silica gel to obtain the 2-benzoxepin compound. The method is simple in reaction operation, mild in reaction condition, relatively high in yield, environment-friendly and suitable for large-scale industrialized production.

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