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873-76-7

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873-76-7 Usage

Description

It is usually used as the intermediate in organic synthesis and pharmaceutical industry. Specifically, this chemical can react with o-xylene in the presence of HAuCl4 or AuCl3 at 80 ℃ to generate the corresponding benzylated product.1 Moreover, the acetylation of 4-chlorobenzyl alcohol in presence of catalytic amounts of Ce(OTf)4 has been performed in acetic acid to produce the desired esters in the excellent yields.2 In addition, this chemical may function as the raw material to produce its corresponding carboxylic acids and ketones in good yields through the oxidation reaction by using hydrogen peroxide and cobalt(Ⅱ) complex.3 Besides, the formylation and acetylation of 4-chlorobenzyl alcohol may be carried out in the presence of Silphos [PCl3?n(SiO2)n] in ethyl formate and ethyl acetate.4

Referrence

Mertins, K.; Lovel, I.; Kischel, J.; Zapf, A.; Beller, M., Gold-catallyzed benzylation of arenes and heteroarenes. Adv. Synth. Catal. 2006, 348, 691-695. Iranpoor, N.; Shekarriz, M., Catalytic Esterification of Alcohols, Carboxylic Acids and Transesterification Reactions with Cerium(IV) Triflate. Bull. Chem. Soc. Jpn. 1999, 72, 455-458. Das, S.; Punniyamurthy, T., Cobalt(II)-catalyzed oxidation of alcohols into carboxylic acids and ketones with hydrogen peroxide. Tetrahedron Lett. 2003, 44, 6033-6035. Iranpoor, N.; Firouzabadi, H.; Jamalian, A., Silphos PCl3-n(SiO2)(n) : a heterogeneous phosphine reagent for formylation and acetylation of alcohols and amines with ethyl formate and acetate. Tetrahedron Lett. 2005, 46, 7963-7966.

Chemical Properties

white crystalline powder

Uses

Different sources of media describe the Uses of 873-76-7 differently. You can refer to the following data:
1. Reagent for carboxyl group protection.
2. 4-Chlorobenzyl alcohol acts as a reagent for the protection of carboxyl groups as their 4-chlorobenzyl esters, more stable to acid than the corresponding benzyl esters. It is used as solvent in paint stripper and waterborne coatings. It acts as curing agent. It is also used in pharmaceuticals, cosmetics, preservatives, and flavoring & fragrance agents.

Check Digit Verification of cas no

The CAS Registry Mumber 873-76-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,7 and 3 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 873-76:
(5*8)+(4*7)+(3*3)+(2*7)+(1*6)=97
97 % 10 = 7
So 873-76-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H7ClO/c8-7-3-1-6(5-9)2-4-7/h1-4,9H,5H2

873-76-7 Well-known Company Product Price

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  • Alfa Aesar

  • (A11504)  4-Chlorobenzyl alcohol, 99%   

  • 873-76-7

  • 25g

  • 489.0CNY

  • Detail
  • Alfa Aesar

  • (A11504)  4-Chlorobenzyl alcohol, 99%   

  • 873-76-7

  • 100g

  • 1368.0CNY

  • Detail
  • Alfa Aesar

  • (A11504)  4-Chlorobenzyl alcohol, 99%   

  • 873-76-7

  • 500g

  • 5751.0CNY

  • Detail
  • Sigma-Aldrich

  • (50754)  4-Chlorobenzylalcohol  analytical standard

  • 873-76-7

  • 50754-100MG

  • 600.21CNY

  • Detail

873-76-7SDS

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 4-Chlorobenzyl Alcohol

1.2 Other means of identification

Product number -
Other names (4-chlorophenyl)methanol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:873-76-7 SDS

873-76-7Synthetic route

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With magnesium(II) perchlorate; polymer-bound NADH (2a) In acetonitrile; benzene at 80℃; for 120h; Further byproducts given;100%
With diisopropoxytitanium(III) tetrahydroborate In dichloromethane at -20℃; for 0.133333h;100%
With zirconium dioxide hydrate; isopropyl alcohol at 60℃; for 0.133333h; Meerwein-Ponndorf-Verley Reduction;100%
para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With C25H42N6Rh(1+)*CF3O3S(1-); phenylsilane In tetrahydrofuran at 30℃; for 20h; Inert atmosphere;100%
With samarium diiodide; benzaldehyde; samarium(III) trifluoromethanesulfonate In tetrahydrofuran; methanol; water at 20℃; for 0.0166667h; Reduction;99%
With samarium diiodide; phosphoric acid In tetrahydrofuran for 0.000833333h; Ambient temperature;94%
Methyl 4-chlorobenzoate
1126-46-1

Methyl 4-chlorobenzoate

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With C39H39N6ORu(1+)*Br(1-); potassium methanolate; hydrogen In tetrahydrofuran at 70℃; under 37503.8 Torr; for 4h; Reagent/catalyst;100%
With C56H70Cl3N10Ru2(1+)*F6P(1-); potassium tert-butylate; hydrogen In tetrahydrofuran; dodecane at 70℃; under 37503.8 Torr; for 16h; Inert atmosphere; Glovebox; Autoclave;100%
With C13H34BFeNOP2; hydrogen In tetrahydrofuran at 60℃; under 22502.3 Torr; for 18h; Autoclave; Inert atmosphere;99%
4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With N-methylpyrrolidine zinc borohydride In tetrahydrofuran at 20℃; for 1.16667h;100%
With Zr(BH4)2Cl2(dabco)2 In tetrahydrofuran for 1.7h; Heating;98%
With sodium tetrahydroborate; lithium perchlorate In acetonitrile for 0.666667h;95%
4-chlorobenzoic anhydride
790-41-0

4-chlorobenzoic anhydride

A

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

B

para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate In tetrahydrofuran for 1h; Ambient temperature;A 94%
B 100%
sodium tetrakis(4-chlorobenzyloxy)borate

sodium tetrakis(4-chlorobenzyloxy)borate

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With water100%
2-(4-chlorobenzyloxy)tetrahydro-2H-pyran
18484-03-2

2-(4-chlorobenzyloxy)tetrahydro-2H-pyran

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
silica-supported prop-1-ylsulfonic acid In methanol99.4%
With sulfuric acid; silica gel In methanol at 20℃; for 0.5h;98%
With lithium borohydride In methanol at 20℃; for 0.416667h;96%
4-chlorobenzamide
619-56-7

4-chlorobenzamide

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With samarium diiodide; water In tetrahydrofuran for 0.00277778h; Ambient temperature;99%
With C24H20ClN2OPRu; potassium tert-butylate; hydrogen In tetrahydrofuran at 110℃; under 10640.7 Torr; for 36h; Inert atmosphere; Schlenk technique;85%
With [fac-8-(2-diphenylphosphinoethyl)aminotrihydroquinoline]RuH(η1-BH4)(CO); hydrogen In isopropyl alcohol at 140℃; under 37503.8 Torr; for 24h; Autoclave;62 %Chromat.
ethyl 4-chlorobenzoate
7335-27-5

ethyl 4-chlorobenzoate

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With sodium tetrahydroborate; hafnium tetrachloride In tetrahydrofuran at 20℃; for 5.6h; Inert atmosphere; Cooling with ice;98%
With phenylsilane; potassium tert-butylate; water; sodium triethylborohydride; cobalt(II) chloride In 1,4-dioxane; toluene at 60℃; for 15h; Inert atmosphere; Glovebox; Schlenk technique;98%
With C30H34Cl2N2P2Ru; potassium methanolate; hydrogen In tetrahydrofuran at 100℃; under 38002.6 - 76005.1 Torr; for 15h; Glovebox; Autoclave;96%
4-chlorobenzyl acetate
5406-33-7

4-chlorobenzyl acetate

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With methanol; potassium permanganate at 25℃; chemoselective reaction;98%
With methanol; [Dy2((2-hydroxy-3-methoxyphenyl)methylene benzohydrazide)2(triflate)2(H2O)4] for 40h; Reflux; Inert atmosphere; chemoselective reaction;81%
With water In acetonitrile for 0.166667h; Quantum yield; Irradiation;
4-chlorobenzyltrimethylsilyl ether
14856-74-7

4-chlorobenzyltrimethylsilyl ether

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With poly (ethylene glycol)-sulfonated sodium montmorillonite nanocomposite In methanol at 20℃; for 0.0333333h;98%
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0666667h; Green chemistry;96%
With rice husk ash supported on anatase-phase titania nanoparticles nanocomposite In methanol at 20℃; for 0.05h;96%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

A

(4'-chlorobenzyl) 4-chlorobenzoate
19048-85-2

(4'-chlorobenzyl) 4-chlorobenzoate

B

N-benzyl-4-chloro-N-methylbenzamide
137374-28-8

N-benzyl-4-chloro-N-methylbenzamide

C

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
tris(bis(trimethylsilyl)amido)lanthanum(III) In benzene-d6 at 25℃; for 24h;A n/a
B 98%
C n/a
1-chloro-4-[(methoxymethoxy)methyl]benzene
1200-16-4

1-chloro-4-[(methoxymethoxy)methyl]benzene

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With 1-methylimidazole hydrogen sulfate at 120℃; for 0.0166667h; Microwave irradiation; chemoselective reaction;97%
phosphotungstic acid In ethanol for 4.5h; Heating;87%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

aniline
62-53-3

aniline

A

4-chlorobenzanilide
6833-15-4

4-chlorobenzanilide

B

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
Stage #1: aniline With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
Stage #2: 4-chlorobenzaldehyde With yttrium(III) chloride In toluene at 20℃; for 48h; Cannizzaro reaction; Inert atmosphere;
Stage #3: With hydrogenchloride In water; toluene at 20℃; Inert atmosphere;
A 97%
B n/a
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

isopropyl alcohol
67-63-0

isopropyl alcohol

A

acetone
67-64-1

acetone

B

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With titanium(IV) oxide at 24.84℃; Meerwein-Ponndorf-Verley Reduction; Sealed tube; UV-irradiation; Inert atmosphere; Green chemistry; chemoselective reaction;A 96%
B 87%
C13H13ClOSi

C13H13ClOSi

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With sodium hydroxide In water Schlenk technique; Inert atmosphere;96%
With water; sodium hydroxide In benzene-d6 at 20℃; Glovebox; Inert atmosphere;
With sodium hydroxide In methanol for 2h;
With sodium hydroxide In water
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

A

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

B

para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

Conditions
ConditionsYield
Stage #1: 4-chlorobenzaldehyde With potassium hydroxide for 0.0833333h; Cannizzaro Reaction; Milling; Inert atmosphere; Sealed tube; Green chemistry;
Stage #2: With hydrogenchloride In water Green chemistry;
A 95%
B 95%
With sodium hydroxide In water at 20℃; for 3.5h; Cannizzaro Reaction;A n/a
B 89%
With TEA; magnesium bromide In dichloromethane at 20℃; for 48h; Cannizzaro reaction;A 88%
B n/a
4-chloro-1-[(ethoxymethoxy)methyl]benzene
1202-68-2

4-chloro-1-[(ethoxymethoxy)methyl]benzene

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With 1-methylimidazole hydrogen sulfate at 120℃; for 0.0166667h; Microwave irradiation; chemoselective reaction;95%
phosphotungstic acid In ethanol for 4.5h; Heating;87%
benzyloxy-trimethylsilane
14642-79-6

benzyloxy-trimethylsilane

4-chloro-1-[(ethoxymethoxy)methyl]benzene
1202-68-2

4-chloro-1-[(ethoxymethoxy)methyl]benzene

A

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

B

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With 1-methylimidazole hydrogen sulfate at 120℃; for 0.0166667h; Microwave irradiation; chemoselective reaction;A 95%
B 10%
Benzyl acetate
140-11-4

Benzyl acetate

4-chloro-1-[(ethoxymethoxy)methyl]benzene
1202-68-2

4-chloro-1-[(ethoxymethoxy)methyl]benzene

A

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

B

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With 1-methylimidazole hydrogen sulfate at 120℃; for 0.0166667h; Microwave irradiation; chemoselective reaction;A 95%
B 20%
4-chlorobenzaldehyde p-toluenesulfonylhydrazone
19350-69-7

4-chlorobenzaldehyde p-toluenesulfonylhydrazone

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With water; potassium carbonate at 130℃; for 0.166667h; Microwave irradiation;95%
C15H22BClO

C15H22BClO

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With sodium hydroxide In water Inert atmosphere;95%
2-((4-chlorobenzyl)oxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1143018-85-2

2-((4-chlorobenzyl)oxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With silica gel at 25℃; Inert atmosphere; Glovebox;95%
With silica gel In methanol for 4h; Reflux;94%
With silica gel In hexane; ethyl acetate92%
4-[(chlorophenyl)methoxy](1,1-dimethylethyl)dimethylsilane
256521-85-4

4-[(chlorophenyl)methoxy](1,1-dimethylethyl)dimethylsilane

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With hafnium tetrakis(trifluoromethanesulfonate) In methanol at 20℃; for 7h;95%
With hafnium tetrakis(trifluoromethanesulfonate) In methanol at 20℃; for 7h;95%
With methanol at 20℃; for 2.33333h;95%
4-chlorobenzoyl azide
21368-28-5

4-chlorobenzoyl azide

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With zinc(II) tetrahydroborate In 1,2-dimethoxyethane for 5.5h; Ambient temperature;94%
With Ca(BH2S3)2 In tetrahydrofuran for 2h; Heating;87%
p-hydroxymethylphenylboronic acid
59016-93-2

p-hydroxymethylphenylboronic acid

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With N-chloro-succinimide; copper(l) chloride In acetonitrile at 80℃; for 12h;94%
With N-chloro-succinimide In acetonitrile at 80℃; for 16h;93%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-n-methylphenylacetylene
766-97-2

4-n-methylphenylacetylene

A

1-(4-chlorophenyl)-3-(4-methylphenyl)prop-2-yn-1-one

1-(4-chlorophenyl)-3-(4-methylphenyl)prop-2-yn-1-one

B

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With triethylamine; zinc(II) iodide In toluene at 80℃; for 12h; Schlenk technique; Inert atmosphere;A 94%
B n/a
4-chlorobenzyl β-(trimethylsilyl)ethoxymethyl ether

4-chlorobenzyl β-(trimethylsilyl)ethoxymethyl ether

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With carbon tetrabromide In isopropyl alcohol for 2h; Heating;93%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

A

1,2-bis(4-chlorophenyl)-1,2-ethandiol
37580-81-7, 67111-67-5, 69483-09-6, 116262-76-1, 38152-44-2

1,2-bis(4-chlorophenyl)-1,2-ethandiol

B

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With vanadium(II) chloride In ethanol; water at 16 - 22℃; for 0.416667h; sonication;A 92%
B 2%
With ammonium chloride; magnesium Ambient temperature;A 90%
B 7%
With zinc(II) chloride; zinc In tetrahydrofuran; water for 3h; Ambient temperature;A 16%
B 82%
acetophenone
98-86-2

acetophenone

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

3-(4-chlorophenyl)-1-phenylpropan-1-one
5739-39-9

3-(4-chlorophenyl)-1-phenylpropan-1-one

Conditions
ConditionsYield
With titanium(IV) oxide; potassium hydroxide In toluene at 100℃; for 10h; Sealed tube; Irradiation;100%
With C27H24Cl3F6IrN2; potassium hydroxide In toluene at 130℃; for 2h;94%
With C16H14IrN2O3; caesium carbonate In tert-Amyl alcohol for 6h; Reflux;91%
para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With oxygen; perruthenate modified mesoporous silicate MCM-41 In toluene at 80℃; for 1h; Oxidation;100%
With n-butyltriphenylphosphonium permanganate In acetonitrile at 20℃; for 0.25h;100%
With butyltriphenylphosphonium chlorochromate In acetonitrile for 0.75h; Heating;100%
para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

1-Chloro-4-(chloromethyl)benzene
104-83-6

1-Chloro-4-(chloromethyl)benzene

Conditions
ConditionsYield
With tetrachloromethane; cross-linked polymer (containing 2.50 mmol of phosphine/g) for 3h; Heating;100%
With ziconium(IV) oxychloride octahydrate; lithium chloride In ethanol; water at 90℃; for 1.5h;95%
With 1,3,5-trichloro-2,4,6-triazine; dimethyl sulfoxide at 20℃; for 0.25h; chemoselective reaction;94%
1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

4-chlorobenzyltrimethylsilyl ether
14856-74-7

4-chlorobenzyltrimethylsilyl ether

Conditions
ConditionsYield
With aluminum potassium sulfate dodecahydrate In acetonitrile at 20℃; for 0.333333h;100%
With 1,3-disulfonic acid imidazolium hydrogen sulfate In neat (no solvent) at 20℃; for 0.0166667h; Green chemistry;100%
With asymmetric salen type di-Schiff base-based zinc complex supported on Fe3O4 nanoparticles at 20℃; for 0.2h;100%
acetic anhydride
108-24-7

acetic anhydride

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

4-chlorobenzyl acetate
5406-33-7

4-chlorobenzyl acetate

Conditions
ConditionsYield
(NH4)8[CeW10O36]*20H2O for 0.0833333h; Heating;100%
With SBA-15-Ph-Pr-SO3H at 20℃; for 0.333333h;100%
With tin(IV) tetraphenylporphyrin perchlorate at 20℃; for 0.0833333h;99%
para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

Conditions
ConditionsYield
With bromine; oxygen In acetonitrile for 10h; Irradiation;100%
With periodic acid; tripropylammonium fluorochromate (VI) In acetonitrile at 0℃;99%
With silica-supported Jones reagent In dichloromethane for 0.035h;99.4%
Dimethoxymethane
109-87-5

Dimethoxymethane

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

1-chloro-4-[(methoxymethoxy)methyl]benzene
1200-16-4

1-chloro-4-[(methoxymethoxy)methyl]benzene

Conditions
ConditionsYield
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide at 20℃; for 1.2h;100%
With zirconyl triflate at 20℃; for 0.166667h; neat (no solvent); chemoselective reaction;100%
With 12-tungstophosphoric acid immobilized on [bmim][FeCl4] at 75 - 82℃; for 0.00555556h; Microwave irradiation;98%
para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

Conditions
ConditionsYield
With ammonium hydroxide; oxygen In tert-Amyl alcohol at 130℃; under 3750.38 Torr; for 24h;100%
Stage #1: para-Chlorobenzyl alcohol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; iodine In dichloromethane at 20℃; for 1h; Inert atmosphere;
Stage #2: With ammonia; iodine In dichloromethane; water at 20℃; for 2h; Inert atmosphere;
99%
With ammonia; oxygen In tert-Amyl alcohol; water at 100℃; under 3750.38 Torr; for 5h; Autoclave; High pressure;99%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

4-chlorobenzoic acid N-hydroxysuccinimide ester
68388-09-0

4-chlorobenzoic acid N-hydroxysuccinimide ester

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; benzoic acid In ethyl acetate for 0.5h; cooling;100%
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In decane; acetonitrile at 80℃; for 18h; Solvent;92%
With tert.-butylhydroperoxide; oxygen In acetonitrile for 24h; Irradiation; Sealed tube;52%
para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

diisopropyl-carbodiimide
693-13-0

diisopropyl-carbodiimide

C14H21ClN2O

C14H21ClN2O

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) at 100℃; for 0.0833333h; Microwave irradiation;100%
C14H17N3O3*ClH

C14H17N3O3*ClH

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

4-chlorobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylate
1144035-02-8

4-chlorobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylate

Conditions
ConditionsYield
Stage #1: para-Chlorobenzyl alcohol; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 3h;
Stage #2: C14H17N3O3*ClH In N,N-dimethyl-formamide at 20℃; for 18h;
100%
1-Phenylethanol
98-85-1, 13323-81-4

1-Phenylethanol

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

3-(4-chlorophenyl)-1-phenylpropan-1-one
5739-39-9

3-(4-chlorophenyl)-1-phenylpropan-1-one

Conditions
ConditionsYield
With Cu-Ag supported on hydrotalcite In o-xylene at 150℃; for 8h; Inert atmosphere;100%
With C44H35ClO4P2Ru; potassium hydroxide In para-xylene at 130℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Molecular sieve;95%
With C44H35ClO4P2Ru; sodium sulfate; potassium hydroxide In toluene at 150℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction;95%
L-valine
72-18-4

L-valine

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

(S)-1-((4-chlorobenzyl)oxy)-3-methyl-1-oxobutan-2-aminium 4-methylbenzenesulfonate

(S)-1-((4-chlorobenzyl)oxy)-3-methyl-1-oxobutan-2-aminium 4-methylbenzenesulfonate

Conditions
ConditionsYield
In water; toluene for 24h; Reflux; Dean-Stark;100%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

2-(4-chlorobenzyloxy)tetrahydro-2H-pyran
18484-03-2

2-(4-chlorobenzyloxy)tetrahydro-2H-pyran

Conditions
ConditionsYield
silica-supported prop-1-ylsulfonic acid In acetonitrile for 0.166667h;99.9%
With chloromethylated polystyrene supported tetrakis(p-aminophenyl)porphyrinatotin(IV) trifluoromethanesulfonate In tetrahydrofuran at 20℃; for 0.1h;99%
With mesoporous p-hydroxybenzenesulphonic acid-formaldehyde polymer resin In neat (no solvent) at 20℃; for 1.15h; chemoselective reaction;97%
L-phenylalanine
63-91-2

L-phenylalanine

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

phenylalanine p-chlorobenzyl ester p-toluenesulfonate

phenylalanine p-chlorobenzyl ester p-toluenesulfonate

Conditions
ConditionsYield
In toluene for 5h; Heating;99.5%
4-chloro-aniline
106-47-8

4-chloro-aniline

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

4-chloro-N-(4-chlorobenzyl)aniline
13159-74-5

4-chloro-N-(4-chlorobenzyl)aniline

Conditions
ConditionsYield
With sodium hydrogencarbonate In toluene at 110℃; for 48h; Inert atmosphere;99%
Stage #1: 4-chloro-aniline; para-Chlorobenzyl alcohol With (1,3-bis(2,6-di-iso-propylphenyl)-4,5-dihydroimidazol-2-ylidene) copper chloride; potassium tert-butylate; oxygen In tetrahydrofuran at 20℃; for 6h; Molecular sieve;
Stage #2: With (1,3-bis(2,6-di-iso-propylphenyl)-4,5-dihydroimidazol-2-ylidene) copper chloride In tetrahydrofuran at 20℃; for 8h; Molecular sieve;
94%
With C51H40Cl2N2O3P2Ru; potassium hydroxide In toluene at 120℃; for 14h;84%
para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With hydrazine hydrate; C23H40MnNO2P2; potassium tert-butylate In tert-butyl alcohol at 115℃; for 48h; Wolff-Kishner Reduction; Green chemistry;99%
With carbon monoxide; hydrogen; benzene at 190℃; under 176522 Torr; Reagens 4: Octacarbonyldikobalt, Reagens 5: Kobaltcarbonat;
With 2,4,6-trimethyl-pyridine; 4,4'-dimethoxyphenyl disulfide; iridium(lll) bis[2-(2,4-difluorophenyl)-5-methylpyridine-N,C20]-4,40-di-tert-butyl-2,20-bipyridine hexafluorophosphate; triphenylphosphine In toluene for 24h; Irradiation;74 %Chromat.
para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

4-chlorobenzyl bromide
622-95-7

4-chlorobenzyl bromide

Conditions
ConditionsYield
Stage #1: para-Chlorobenzyl alcohol With 1,2,3-Benzotriazole; thionyl chloride In dichloromethane
Stage #2: With potassium bromide In dichloromethane; N,N-dimethyl-formamide for 0.266667h;
99%
With N-Bromosuccinimide; triphenylphosphine for 0.00277778h; microwave irradiation;98%
With bromine; triphenylphosphine In dichloromethane at -78 - 20℃; for 18h; Inert atmosphere;97%
para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

1-chloro-4-(iodomethyl)benzene
35424-56-7

1-chloro-4-(iodomethyl)benzene

Conditions
ConditionsYield
Stage #1: para-Chlorobenzyl alcohol With 1,2,3-Benzotriazole; thionyl chloride In dichloromethane
Stage #2: With potassium iodide In dichloromethane; N,N-dimethyl-formamide for 0.0833333h;
99%
With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; hydrogen; iodine; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dichloro-ethane at 20℃; under 22502.3 Torr; Autoclave; Schlenk technique;99%
With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; Ru(OCOCH3)2{(S)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl)}; hydrogen; iodine In toluene at 20℃; under 22502.3 Torr; for 5.5h;99%
para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

C20H21N3O6S
194664-25-0

C20H21N3O6S

1-benzyloxycarbonyl-2-tert-butyloxycarbonyl-1-(4-chlorobenzyl)-2-(4-cyanobenzenesulfonyl)-hydrazine
194664-26-1

1-benzyloxycarbonyl-2-tert-butyloxycarbonyl-1-(4-chlorobenzyl)-2-(4-cyanobenzenesulfonyl)-hydrazine

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran99%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Mitsunobu reaction;99%
acetic acid
64-19-7

acetic acid

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

4-chlorobenzyl acetate
5406-33-7

4-chlorobenzyl acetate

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate at 20℃; for 0.583333h;99%
With potassium fluoride at 80℃; for 3h;97%
With 50wtpercent Cs2.5H0.5PW12O40 supported on MCM-41 In acetonitrile at 50℃; for 0.5h;97%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

2-Nitrobenzenesulfonyl chloride
1694-92-4

2-Nitrobenzenesulfonyl chloride

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

(S)-2-[(4-Chloro-benzyl)-(2-nitro-benzenesulfonyl)-amino]-propionic acid

(S)-2-[(4-Chloro-benzyl)-(2-nitro-benzenesulfonyl)-amino]-propionic acid

Conditions
ConditionsYield
Multistep reaction;99%

873-76-7Relevant articles and documents

Hydrogenation of Esters by Manganese Catalysts

Li, Fu,Li, Xiao-Gen,Xiao, Li-Jun,Xie, Jian-Hua,Xu, Yue,Zhou, Qi-Lin

, (2022/01/13)

The hydrogenation of esters catalyzed by a manganese complex of phosphine-aminopyridine ligand was developed. Using this protocol, a variety of (hetero)aromatic and aliphatic carboxylates including biomass-derived esters and lactones were hydrogenated to primary alcohols with 63–98% yields. The manganese catalyst was found to be active for the hydrogenation of methyl benzoate, providing benzyl alcohol with turnover numbers (TON) as high as 45,000. Investigation of catalyst intermediates indicated that the amido manganese complex was the active catalyst species for the reaction. (Figure presented.).

A mild and selective Cu(II) salts-catalyzed reduction of nitro, azo, azoxy, N-aryl hydroxylamine, nitroso, acid halide, ester, and azide compounds using hydrogen surrogacy of sodium borohydride

Kalola, Anirudhdha G.,Prasad, Pratibha,Mokariya, Jaydeep A.,Patel, Manish P.

supporting information, p. 3565 - 3589 (2021/10/12)

The first mild, in situ, single-pot, high-yielding well-screened copper (II) salt-based catalyst system utilizing the hydrogen surrogacy of sodium borohydride for selective hydrogenation of a broad range of nitro substrates into the corresponding amine under habitancy of water or methanol like green solvents have been described. Moreover, this catalytic system can also activate various functional groups for hydride reduction within prompted time, with low catalyst-loading, without any requirement of high pressure or molecular hydrogen supply. Notably, this system explores a great potential to substitute expensive traditional hydrogenation methodologies and thus offers a greener and simple hydrogenative strategy in the field of organic synthesis.

Redox-active ligand based Mn(i)-catalyst for hydrosilylative ester reduction

Chakraborty, Soumi,Das, Arpan,Mandal, Swadhin K.

supporting information, p. 12671 - 12674 (2021/12/04)

Herein a Mn(i) catalyst bearing a redox-active phenalenyl (PLY) based ligand is reported for the efficient hydrosilylation of esters to alcohols using the inexpensive silane source polymethylhydrosiloxane (PMHS) under mild conditions. Mechanistic investigations suggest a strong ligand-metal cooperation where a ligand-based single electron transfer (SET) process initiates the reaction through Si-H bond activation.

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