102-20-5

Basic information

• Product Name: Phenethyl phenylacetate
• Synonyms: PHENETHYL PHENYLACETATE 98+% FCC;2-Phenethyl phenylacetate;2-Phenylethyl α-toluate;Benzylcarbinyl α-toluate;Phenethylphenylacetat;PHENYLETHYLPHENYLACETAT;2-Phenylethyl 2-phenylacetate;Benzylcarbinyl a-toluate
• CAS NO: 102-20-5
• Molecular Formula: C₁₆H₁₆O₂
• Molecular Weight: 240.3
• EINECS: 203-013-1
• Product Categories: API intermediates
• Mol File: 102-20-5.mol
• Article Data: 39

Chemical Properties

• Melting Point: 28 °C(lit.)
• Boiling Point: 325 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.082 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.3E-05mmHg at 25°C
• Refractive Index: n20/D 1.55(lit.)
• Solubility: 1g/L in organic solvents at 20 ℃
• PKA: 0[at 20 ℃]
• Water Solubility: 15.56-22mg/L at 20-22℃
• CAS DataBase Reference: Phenethyl phenylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Phenethyl phenylacetate(102-20-5)
• EPA Substance Registry System: Phenethyl phenylacetate(102-20-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: AJ3255000
• Hazardous Substances Data: 102-20-5(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 102-20-5 differently. You can refer to the following data:
1. Colorless to pale yellow liquid or crystalline solid
2. Phenylethyl Phenylacetate has been identified in, for example, the flower concrete of Michelia champaca L. It is a colorless liquid or in the form of crystals (mp 26.5°C), which have a heavy, sweet, rose or hyacinth odor and a distinct honey note. The ester is used particularly in floral fragrance compositions and as a fixative.
3. Phenethyl phenylacetate has a heavy, sweet, floral and balsamic odor, somewhat rosy and a sweet, honey-like flavor.

Occurrence

Has apparently not been reported to occur in nature.

Uses

Different sources of media describe the Uses of 102-20-5 differently. You can refer to the following data:
1. 2-Phenylethyl 2-Phenylacetate is an antimicrobial spray applied freshening compounds for fabric.
2. Phenethyl Phenylacetate is a flavoring agent that is a colorless or pale yellow liquid, with an odor resembling roses and hyacinth, which becomes solid at <26°c (78.8°f). it is soluble in alcohol, insol- uble in water. it is obtained by chemical synthesis.

Preparation

By esterification of phenylacetic acid with phenethyl alcohol in the presence of H2SO4; also by direct esterification in the presence of gaseous HCl.

Taste threshold values

Taste characteristics at 25 ppm: honey, floral, green, rose, cocoa, hay and tropical body.

Flammability and Explosibility

Nonflammable

Safety Profile

Moderately toxic by ingestion. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.

InChI:InChI=1/C16H16O2/c17-16(13-15-9-5-2-6-10-15)18-12-11-14-7-3-1-4-8-14/h1-10H,11-13H2

Synthetic route

2-phenylethanol (60-12-8) → phenyl-acetic acid phenethyl ester (102-20-5) + phenylacetaldehyde (122-78-1)

Conditions	Yield
With silica gel; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate In dichloromethane	A 4% B 99%
With pyridine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; iodine; sodium hydrogencarbonate In dichloromethane; water at 20 - 25℃; for 3h;	A 58.7% B 41.3%
With oxygen at 120℃; for 5h; Neat (no solvent);
With pyridine; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; iodine; sodium hydrogencarbonate In dichloromethane; water at 20 - 22℃; for 3h; Catalytic behavior; Time;	A 71 %Chromat. B 23 %Chromat.
With 2,6-dimethylpyridine; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; iodine; sodium hydrogencarbonate In dichloromethane; water at 20 - 22℃; for 3h; Catalytic behavior; Time;	A 12 %Chromat. B 86 %Chromat.

phenylacetic acid (103-82-2) + 2-phenylethanol (60-12-8) → phenyl-acetic acid phenethyl ester (102-20-5)

Conditions	Yield
With potassium hydroxide	98.6%
With C10H10Zr(2+)*2CF3O3S(1-)*C4H8O at 80℃; for 24h; Sealed tube;	95%
With silica gel-immobilized perchloric acid at 80℃; for 6h; Fischer esterification; Inert atmosphere; Neat (no solvent);	94%

2-phenylethanol (60-12-8) → phenyl-acetic acid phenethyl ester (102-20-5)

Conditions	Yield
With periodic acid; pyridinium chlorochromate In acetonitrile at 0 - 20℃; for 2h;	94%
With sodium bromite In water; acetic acid for 10h; Ambient temperature;	91%
With peracetic acid; sodium bromide In ethyl acetate at 39.9℃; for 2h;	86%

2-phenylethanol (60-12-8) + tert-butylamine (75-64-9) → phenyl-acetic acid phenethyl ester (102-20-5) + 2-methyl-N-phenethylpropan-2-amine (24070-10-8)

Conditions	Yield
With 3 A molecular sieve; potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; [Ru(p-cumene)Cl2]2 In toluene at 110℃; for 24h; Product distribution; Further Variations:; Catalysts;	A 7% B 88%
With 3 A molecular sieve; potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; [Ru(p-cumene)Cl2]2 In toluene at 110℃; for 24h;	A 61% B n/a

phenylacetaldehyde (122-78-1) → phenyl-acetic acid phenethyl ester (102-20-5)

Conditions	Yield
With Rh(PhBP3)(H)2(NCMe); hydrogen In toluene at 20℃; under 760.051 Torr; for 0.166667h; Tishchenko reaction;	85%

2-phenylethanol (60-12-8) + phenylacetylene (536-74-3) → phenylacetic acid (103-82-2) + phenyl-acetic acid phenethyl ester (102-20-5)

Conditions	Yield
With dihydrogen peroxide; methyltrioxorhenium(VII) for 48h;	A 50% B 47%

2-phenylethanol (60-12-8) → phenyl-acetic acid phenethyl ester (102-20-5) + toluene (108-88-3)

Conditions	Yield
With [RuCl2(p-cymene)(iPr2-imy)]; potassium hydroxide; tricyclohexylphosphine In 1,3,5-trimethyl-benzene at 163℃; for 18h; Inert atmosphere;	A 48% B 7%

2-phenylethanol (60-12-8) + di-n-propylamine (142-84-7) → phenyl-acetic acid phenethyl ester (102-20-5) + 2-phenyl-N,N-dipropylacetamide (25173-09-5)

Conditions	Yield
With C15H22Cl2N2Ru; potassium tert-butylate In toluene for 24h; Inert atmosphere; Reflux;	A 21% B 44%

2-phenylethanol (60-12-8) + dibenzylamine (103-49-1) → phenyl-acetic acid phenethyl ester (102-20-5) + N,N-dibenzyl-2-phenylacetamide (102459-18-7)

Conditions	Yield
With C15H22Cl2N2Ru; potassium tert-butylate In toluene for 24h; Inert atmosphere; Reflux;	A 19% B 40%

phenylacetic acid (103-82-2) → 2-phenylethanol (60-12-8) + phenyl-acetic acid phenethyl ester (102-20-5)

Conditions	Yield
With rhenium-catalyst at 149℃; under 117681 Torr; Hydrogenation;
With tin(II) trifluoromethanesulfonate; tris(2,4-pentanedionato)ruthenium(III); hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In water; toluene at 160℃; under 45004.5 Torr; for 48h; Reagent/catalyst; Autoclave;	A 49 %Chromat. B 20 %Chromat.

phenylacetic acid (103-82-2) → phenyl-acetic acid phenethyl ester (102-20-5)

Conditions	Yield
With sulfuric acid bei der elektrolytischen Reduktion an einer Bleikathode;
With tin(II) trifluoromethanesulfonate; tris(2,4-pentanedionato)ruthenium(III); hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In toluene at 160℃; under 45004.5 Torr; for 48h; Reagent/catalyst; Autoclave;	26 %Chromat.

aluminum ethoxide (555-75-9) + phenylacetaldehyde (122-78-1) → phenyl-acetic acid phenethyl ester (102-20-5)

phenylacetyl chloride (103-80-0) → phenyl-acetic acid phenethyl ester (102-20-5)

Conditions	Yield
With triphenylstannane

Ethyl 2-phenylethanoate (101-97-3) → Phenylessigsaeurehexylester (5421-17-0) + phenyl-acetic acid phenethyl ester (102-20-5) + phenylacetic acid octyl ester (122-45-2)

Conditions	Yield
Product distribution; competition reaction with n-hexanol, n-octanol and phenylethanol; selectivity of catalysis with SiO2, also mod. with Ph-CH<(EtO)3SiO>-P(O)(OEt)(OHex) or H2SO4;

diethyl ether (60-29-7) + phenylacetyl chloride (103-80-0) + benzene (71-43-2) + magnesium + magnesium iodide → phenyl-acetic acid phenethyl ester (102-20-5) + acid C18H18O3 of mp: 198 degree

phenylacetic acid (103-82-2) + sulfuric acid (7664-93-9) → phenyl-acetic acid phenethyl ester (102-20-5)

Conditions	Yield
at 70℃; bei der Elektrolyse an einer Bleikathode.Diazotization;

phenylacetic acid (103-82-2) + rhenium → 2-phenylethanol (60-12-8) + phenyl-acetic acid phenethyl ester (102-20-5)

Conditions	Yield
at 150℃; under 117681 Torr; Hydrogenation;

2-phenylethanol (60-12-8) + sulfuric acid (7664-93-9) + dichromate → phenyl-acetic acid phenethyl ester (102-20-5) + benzaldehyde (100-52-7) + acetic acid (64-19-7) + benzoic acid (65-85-0)

2-phenylethanol (60-12-8) + benzyl alcohol (100-51-6) → benzyl 2-phenylacetate (102-16-9) + benzoic acid benzyl ester (120-51-4) + 2-Phenylethyl benzoate (94-47-3) + phenyl-acetic acid phenethyl ester (102-20-5)

Conditions	Yield
With magnesium nitride; [RuCl2(p-cymene)(iPr2-imy)]; potassium tert-butylate; tricyclohexylphosphine tetrafluoroborate In toluene at 110℃; for 24h; Schlenk technique; Inert atmosphere;

1-Phenylethanol (98-85-1, 13323-81-4) + 2-phenylethanol (60-12-8) → phenyl-acetic acid phenethyl ester (102-20-5) + acetophenone (98-86-2)

Conditions	Yield
With magnesium nitride; [RuCl2(p-cymene)(iPr2-imy)]; potassium tert-butylate; tricyclohexylphosphine tetrafluoroborate In toluene at 110℃; for 24h; Schlenk technique; Inert atmosphere;

phenylacetic acid (103-82-2) + 1,1-diphenylethanol (599-67-7) + 2-phenylethanol (60-12-8) + 4-nitrobenzaldehdye (555-16-8) + 4-methoxy-benzaldehyde (123-11-5) + 4-methoxy-aniline (104-94-9) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 1,1-Diphenylethylene (530-48-3) + 4-methoxy-N-(4-nitrobenzylidene)aniline (5455-87-8) + p-methoxybenzaldehyde neopentyl glycol acetal (6290-08-0) + phenyl-acetic acid phenethyl ester (102-20-5) + N-(4-methoxy benzylidene)-4-methoxyaniline (1749-08-2)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 48h; Inert atmosphere; Reflux; Dean-Stark;	A 99 %Spectr. B 75 %Spectr. C 72 %Spectr. D 59 %Spectr. E 5 %Spectr.

...Expand

phenylacetic acid (103-82-2) + 1,1-diphenylethanol (599-67-7) + 2-phenylethanol (60-12-8) + 4-chlorobenzaldehyde (104-88-1) + 4-nitrobenzaldehdye (555-16-8) + 4-methoxy-aniline (104-94-9) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 1,1-Diphenylethylene (530-48-3) + 4-methoxy-N-(4-nitrobenzylidene)aniline (5455-87-8) + 2-(4-chlorophenyl)-5,5-dimethyl-1,3-dioxane (6283-10-9) + 5,5-dimethyl-2-(4-nitro-phenyl)-[1,3]dioxane (838-42-6) + N-(4-chlorobenzylidene)-4-methoxyaniline (1749-03-7) + phenyl-acetic acid phenethyl ester (102-20-5)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 48h; Inert atmosphere; Reflux; Dean-Stark;	A 99 %Spectr. B 52 %Spectr. C 52 %Spectr. D 48 %Spectr. E 43 %Spectr. F 99 %Spectr.

...Expand

phenylacetic acid (103-82-2) + 1,1-diphenylethanol (599-67-7) + 2,4-dinitrobenzaldehyde (528-75-6) + 2-phenylethanol (60-12-8) + 4-chloro-aniline (106-47-8) + 2,2-Dimethyl-1,3-propanediol (126-30-7) + 2,4-Dimethoxybenzaldehyde (613-45-6) → 1,1-Diphenylethylene (530-48-3) + phenyl-acetic acid phenethyl ester (102-20-5) + 2-(2,4-dimethoxyphenyl)-5,5-dimethyl-1,3-dioxane (1620217-69-7) + 4-chloro-N-(2,4-dinitrobenzylidene)aniline (354538-08-2)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 48h; Inert atmosphere; Reflux; Dean-Stark;	A 99 %Spectr. B 99 %Spectr. C 74 %Spectr. D 83 %Spectr.

...Expand

phenylacetic acid (103-82-2) + 1,1-diphenylethanol (599-67-7) + 2,4-dinitrobenzaldehyde (528-75-6) + 2-phenylethanol (60-12-8) + 4-methoxy-aniline (104-94-9) + 2,2-Dimethyl-1,3-propanediol (126-30-7) + phenylboronic acid (98-80-6) → 1,1-Diphenylethylene (530-48-3) + N-(2,4-dinitrobenzylidene)-4-methoxyaniline (354538-06-0) + phenyl-acetic acid phenethyl ester (102-20-5) + 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane (5123-13-7)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 48h; Inert atmosphere; Reflux; Dean-Stark;	A 98 %Spectr. B 93 %Spectr. C 99 %Spectr. D 99 %Spectr.

...Expand

phenylacetic acid (103-82-2) + 1,1-diphenylethanol (599-67-7) + 2,4-dinitrobenzaldehyde (528-75-6) + 2-phenylethanol (60-12-8) + pentafluorophenylboronic acid (1582-24-7) + 4-methoxy-aniline (104-94-9) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 1,1-Diphenylethylene (530-48-3) + N-(2,4-dinitrobenzylidene)-4-methoxyaniline (354538-06-0) + phenyl-acetic acid phenethyl ester (102-20-5) + (2,3,4,5,6-pentafluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane (1262967-46-3)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 48h; Inert atmosphere; Reflux; Dean-Stark;	A 99 %Spectr. B 97 %Spectr. C 99 %Spectr. D 74 %Spectr.

...Expand

phenylacetic acid (103-82-2) + 1,1-diphenylethanol (599-67-7) + 2,4-dinitrobenzaldehyde (528-75-6) + 2-phenylethanol (60-12-8) + 4-methoxy-aniline (104-94-9) + 2,2-Dimethyl-1,3-propanediol (126-30-7) + 2,4-Dimethoxybenzaldehyde (613-45-6) → 1,1-Diphenylethylene (530-48-3) + N-(2,4-dinitrobenzylidene)-4-methoxyaniline (354538-06-0) + phenyl-acetic acid phenethyl ester (102-20-5) + 2-(2,4-dimethoxyphenyl)-5,5-dimethyl-1,3-dioxane (1620217-69-7) + N-(2,4-dimethoxybenzylidene)-4-methoxyaniline (123794-61-6)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 48h; Inert atmosphere; Reflux; Dean-Stark;	A 99 %Spectr. B 84 %Spectr. C 96 %Spectr. D 77 %Spectr. E 9 %Spectr.

...Expand

phenylacetic acid (103-82-2) + 1,1-diphenylethanol (599-67-7) + 2,4-dinitrobenzaldehyde (528-75-6) + 2-phenylethanol (60-12-8) + 2,2-Dimethyl-1,3-propanediol (126-30-7) + aniline (62-53-3) + 2,4-Dimethoxybenzaldehyde (613-45-6) → 1,1-Diphenylethylene (530-48-3) + phenyl-acetic acid phenethyl ester (102-20-5) + 2-(2,4-dimethoxyphenyl)-5,5-dimethyl-1,3-dioxane (1620217-69-7) + 1-(2,4-dinitrophenyl)-N-phenylmethanimine (149742-71-2, 97946-02-6)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 48h; Inert atmosphere; Reflux; Dean-Stark;	A 99 %Spectr. B 98 %Spectr. C 80 %Spectr. D 86 %Spectr.

...Expand

phenylacetic acid (103-82-2) + 1,1-diphenylethanol (599-67-7) + 2,4-dinitrobenzaldehyde (528-75-6) + 2-phenylethanol (60-12-8) + cyclohexylamine (108-91-8) + 2,2-Dimethyl-1,3-propanediol (126-30-7) + 2,4-Dimethoxybenzaldehyde (613-45-6) → 1,1-Diphenylethylene (530-48-3) + phenyl-acetic acid phenethyl ester (102-20-5) + 2-(2,4-dimethoxyphenyl)-5,5-dimethyl-1,3-dioxane (1620217-69-7) + N-(2,4-dinitrobenzylidene)cyclohexanamine (553662-91-2)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 48h; Inert atmosphere; Reflux; Dean-Stark;	A 99 %Spectr. B 43 %Spectr. C 95 %Spectr. D 72 %Spectr.

...Expand

phenylacetic acid (103-82-2) + 1,1-diphenylethanol (599-67-7) + 2,4-dinitrobenzaldehyde (528-75-6) + 2-phenylethanol (60-12-8) + benzaldehyde (100-52-7) + 4-methoxy-aniline (104-94-9) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 1,1-Diphenylethylene (530-48-3) + 5,5-dimethyl-2-phenyl-[1,3]dioxane (776-88-5) + N-(2,4-dinitrobenzylidene)-4-methoxyaniline (354538-06-0) + phenyl-acetic acid phenethyl ester (102-20-5) + [4-(benzylideneamino)phenyl]methanol (783-08-4)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 48h; Inert atmosphere; Reflux; Dean-Stark;	A 99 %Spectr. B 79 %Spectr. C 92 %Spectr. D 98 %Spectr. E 5 %Spectr.

...Expand

methanol (67-56-1) + phenyl-acetic acid phenethyl ester (102-20-5) → benzeneacetic acid methyl ester (101-41-7)

Conditions	Yield
With 1-butyl-3-methylimidazolium tetrachloridoferrate(III) at 146.84℃; for 6h; Reagent/catalyst;	96.6%

phenyl-acetic acid phenethyl ester (102-20-5) → di(2-phenylethyl) ether (2396-53-4)

Conditions	Yield
With triiron dodecarbonyl; 1,1,3,3-Tetramethyldisiloxane In toluene at 100℃; for 2h; Inert atmosphere; Schlenk technique;	85%

phenyl-acetic acid phenethyl ester (102-20-5) + allyl bromide (106-95-6) → phenethyl 2-phenylpent-4-enoate (1181399-18-7)

Conditions	Yield
With caesium hydroxide monohydrate; 2,7-bis[O(9)-allylhydrocinchonidinium-N-methyl]naphthalene dibromide In dichloromethane at -40℃; for 23h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	77%

phenyl-acetic acid phenethyl ester (102-20-5) → 2-phenylethyl 2-oxo-2-phenylacetate (244263-79-4)

Conditions	Yield
Stage #1: phenyl-acetic acid phenethyl ester With tert.-butylhydroperoxide; copper(II) oxide In water at 110℃; for 4.5h; Stage #2: With pyridine In water at 50℃; for 4h;	61%

phenyl-acetic acid phenethyl ester (102-20-5) → styrene (292638-84-7)

Conditions	Yield
at 315 - 320℃;

phenyl-acetic acid phenethyl ester (102-20-5) → styrene (292638-84-7) + phenylacetic acid (103-82-2)

Conditions	Yield
at 315 - 320℃;

phenyl-acetic acid phenethyl ester (102-20-5) + benzylmagnesium chloride (6921-34-2) → tribenzylcarbinol (6712-97-6)

Conditions	Yield
With diethyl ether

phenyl-acetic acid phenethyl ester (102-20-5) → styrene oxide (96-09-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 315 - 320 °C 2: peroxybenzoic acid; chloroform / 0 °C View Scheme

phenyl-acetic acid phenethyl ester (102-20-5) → 2-phenyl-acrylic Acid Phenethyl Ester (880348-56-1)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate; paraformaldehyde In diethyl ether; toluene	1.48 g (60%)

phenyl-acetic acid phenethyl ester (102-20-5) + allyl bromide (106-95-6) → (+/-)-phenethyl 2-phenylpent-4-enoate (1181399-16-5)

Conditions	Yield
With caesium hydroxide monohydrate; tetrabutylammomium bromide In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;

phenyl-acetic acid phenethyl ester (102-20-5) → 2-phenylethanol (60-12-8)

Conditions	Yield
Stage #1: phenyl-acetic acid phenethyl ester With iron (II) stearate; ethylenediamine In toluene at 20℃; for 0.0833333h; Inert atmosphere; Schlenk technique; Stage #2: In toluene at 100℃; for 20h; Inert atmosphere; Schlenk technique;	84 %Chromat.
Stage #1: phenyl-acetic acid phenethyl ester With C33H58FeN3PSi2; phenylsilane In toluene at 20℃; for 4h; Inert atmosphere; Glovebox; Green chemistry; Stage #2: With sodium hydroxide In toluene for 1h; Green chemistry;

Upstream product

• 103-82-2 phenylacetic acid 
• 60-12-8 2-phenylethanol 
• 101-97-3 Ethyl 2-phenylethanoate 
• 536-74-3 phenylacetylene 
• 60-29-7 diethyl ether 
• 103-80-0 phenylacetyl chloride 
• 71-43-2 benzene 
• 7664-93-9 sulfuric acid 
• 142-84-7 di-n-propylamine 
• 103-49-1 dibenzylamine 
• 80-05-7 BPA 
• 5614-37-9 cyclopentyl methyl ether 
• 108-88-3 toluene 
• 1555-80-2 phenylacetic anhydride 

Downstream Products

• 6712-97-6 tribenzylcarbinol 
• 244263-79-4 2-phenylethyl 2-oxo-2-phenylacetate 
• 101-41-7 benzeneacetic acid methyl ester 
• 60-12-8 2-phenylethanol 
• 2396-53-4 di(2-phenylethyl) ether 
• 1181399-18-7 phenethyl 2-phenylpent-4-enoate 
• 1181399-16-5 (+/-)-phenethyl 2-phenylpent-4-enoate 
• 880348-56-1 2-phenyl-acrylic Acid Phenethyl Ester 
• 96-09-3 styrene oxide 
• 100-42-5 styrene 
• 103-82-2 phenylacetic acid 

Relevant articles and documents

Oxidation of Alcohols with Peracetic Acid in Ethyl Acetate in the Presence of Sodium Bromide

Aliphatic primary alcohols and 1,ω-diols were oxidized to the dimeric esters and lactones, respectively, by peracetic acid in ethyl acetate in the presence of sodium bromide under mild conditions.Aliphatic secondary and benzylic alcohols were converted smoothly to the corresponding carbonyl compounds by the same system.

Synthesis of Unsymmetrical N-Heterocyclic Carbene-Nitrogen-Phosphine Chelated Ruthenium(II) Complexes and Their Reactivity in Acceptorless Dehydrogenative Coupling of Alcohols to Esters

Two novel ruthenium complexes RuH(CO)Cl(PPh3)(κ2-CP) (1) and [fac-RuH(CO)(PPh3)(κ3-CNP)]Cl (2) bearing unsymmetrical N-heterocyclic carbene-nitrogen-phosphine (CNP) were synthesized and characterized with 1H NMR, 31P NMR, and HRMS. The structure of complex 2 was further confirmed by single-crystal X-ray diffraction. An anion exchange experiment proved that complex 2 could transform into complex 1 in solution. The two complexes exhibited a highly catalytic performance in acceptorless dehydrogenative coupling of alcohols to esters, and the excellent isolated yields of esters were given in a catalyst loading of 1% for para- and meta-substituted benzyl alcohols and long-chain primary alcohols. Although some ortho-substituted benzyl alcohols displayed a relatively low reactivity due to the steric hindrance and the coordination of electron donor with the ruthenium center, the good product yields were still obtained by prolonging the reaction time. Especially, this system successfully realized the dehydrogenative cross-coupling to esters between two different primary alcohols.

RUTHENIUM CATALYZED TRANSFORMATION OF ALCOHOLS TO ESTERS AND LACTONES

Homogeneous catalytic oxidative condensation of alcohols and diols to their corresponding esters and lactones has been accomplished using RuH2(PPh3)4.

A TEMPO-like nitroxide combined with an alkyl-substituted pyridine: An efficient catalytic system for the selective oxidation of alcohols with iodine

An efficient method for the oxidation of alcohols to aldehydes or ketones in a two-phase CH2Cl2/NaHCO3 (aq.) system, using iodine and catalytic amounts of 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxyl and 2,4,6-trimethylpyridine, was developed. The performance of the method was demonstrated by the selective oxidation of 37 variously substituted alcohols in ≥90% yield, including the gram-scale synthesis of the important chemical 2,5-diformylfuran from biomass-derived 5-hydroxylmethylfurfural.

Pyridinium chlorochromate catalyzed oxidation of alcohols to aldehydes and ketones with periodic acid

A facile pyridinium chlorochromate (PCC) catalyzed (2 mol %) oxidation of alcohols to ketones and aldehydes using 1.05 equiv of H5IO 6 in acetonitrile is described here.

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Staudinger’s phosphazene as an efficient esterifying reagent

A new application of Staudinger’s phosphazene as an efficient esterifying reagent is reported. Staudinger’s phosphazene formed in situ by the reaction of organic mono-azide with triphenylphosphine, which is trapped by carboxylic acid, to afford amide exclusively. In contrast, interestingly the same phosphazene behaves in a different way as an efficient esterifying reagent, affording ester under a solvent-free microwave-assisted protocol wherein alcohol is added as the another component in addition to the other reactants. This discovery adds yet another new application of Staudinger’s phosphazene to synthetic chemistry.

Aldehyde effect and ligand discovery in Ru-catalyzed dehydrogenative cross-coupling of alcohols to esters

The presence of different aldehydes is found to have a significant influence on the catalytic performance when using PN(H)P type ligands for dehydrogenation of alcohols. Accordingly, hybrid multi-dentate ligands were discovered based on an oxygen-transfer alkylation of PNP ligands by aldehydes. The relevant Ru-PNN(PO) system provided the desired unsymmetrical esters in good yields via acceptorless dehydrogenation of alcohols. Hydrogen bonding interactions between the phosphine oxide moieties and alcohol substrates likely assisted the observed high chemoselectivity.