Phenylacetic acid methyl ester

Structural formula
General
Surname	Phenylacetic acid methyl ester
other names	Methyl α-toluate; Methyl phenyl acetate;
Molecular formula	C 9 H 10 O 2
Brief description	colorless liquid with a sweet odor
External identifiers / databases
EC number	202-940-9
ECHA InfoCard	100.002.674
PubChem	7559
Wikidata	Q390681
properties
Molar mass	150.18 g · mol -1
Physical state	liquid
density	1.07 g cm −3 (20 ° C)
boiling point	218 ° C
Vapor pressure	17 Pa (20 ° C)
solubility	practically insoluble in water (923 mg l −1 at 20 ° C)
Refractive index	1.503 (20 ° C)
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Phenylacetic acid methyl ester is the ester of phenylacetic acid with methanol . It is a liquid that smells pleasantly of honey .

presentation

The synthesis of methyl phenylacetate is achieved via the esterification of phenylacetic acid . The esterification can be carried out in various ways. These include the acidic alcoholic esterification with methanol and hydrochloric acid (HCl)

{\ displaystyle \ mathrm {Ph {-} CH_ {2} {-} COOH \ + \ CH_ {3} OH \ {\ xrightarrow {HCl}} \ \ Ph {-} CH_ {2} {-} COOCH_ {3 } \ + \ H_ {2} O}}

Ph = phenyl

the esterification of the acid chloride of phenylacetic acid with methanol

{\ displaystyle \ mathrm {Ph {-} CH_ {2} {-} COCl \ + \ CH_ {3} OH \ {\ xrightarrow {LS}} \ \ Ph {-} CH_ {2} {-} COOCH_ {3 } \ + \ HCl}}

Ph = phenyl, LS = Lewis acid

as well as the oxidation of benzyl chloride .

properties

Phenylacetic acid methyl ester is a colorless liquid. The boiling point at normal pressure is 217 ° C. According to Antoine, the vapor pressure function results from log ₁₀ (P) = A− (B / (T + C)) (P in bar, T in K) with A = 3.899, B = 1545 and C = −87.84 in the temperature range from 60 to 160 ° C. The heat of vaporization at 25 ° C is 57.36 kJ mol ⁻¹ . The flash point is 91 ° C.

use

Phenylacetic acid methyl ester is used for the production of perfumes and aromas (honey aroma).

Web links

Entry on Methyl phenylacetate at ChemBlink , accessed February 25, 2011.
Entry on methyl 2-phenylacetate at thegoodscentscompany.com

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry on methyl (phenyl acetate) in the GESTIS substance database of the IFA , accessed on January 21, 2020(JavaScript required) .
↑ ^a ^b Data sheet methyl phenylacetate from Sigma-Aldrich , accessed on May 9, 2017 ( PDF ).
↑ B. Radziszewski: About some derivatives of phenylacetic acid , in: Chemischeberichte , 1969 , 2 , pp. 207-210; doi : 10.1002 / cber.18690020198 .
^ RA Aitken, MC Bibby, PA Cooper, JA Double, AL Laws, RB Ritchie, DWJ Wilson: Synthesis and Antitumour Activity of New Derivatives of Flavone-8-Acetic Acid (FAA). Part 4: Variation of the Basic Structure , in: Archiv der Pharmazie , 2000 , 333 , pp. 181–188; doi : 10.1002 / 1521-4184 (20006) 333: 6 <181 :: AID-ARDP181> 3.0.CO; 2-O .
↑ K. Ogura, N. Yahata, K. Hashizume, K. Tsuyama, K. Takahashi, H. Iida: Utilization of Methylthiomethyl p-toluyl sulfone in organic synthesis , in: Chemistry Letters , 1983 , 12 , pp. 767-770 .
↑ Lecat, M .: New binary azeotropes: 6th list in Ann. Soc. Sci. Bruxelles, Ser. B, 47 (1927) 63-71.
↑ ^a ^b Hoskovec, M .; Grygarova, D .; Cvacka, J .; Streinz, L .; Zima, J .; Verevkin, SP; Koutek, B .: Determining the vapor pressures of plant volatiles from gas chromatographic retention data in J. Chrom. A 1083 (2005) 161–172, Antoine parameters by conversion from the Kirchhoff-Rankin equation.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f Entry on methyl (phenyl acetate) in the GESTIS substance database of the IFA , accessed on January 21, 2020(JavaScript required) .

[Sigma-2] Data sheet methyl phenylacetate from Sigma-Aldrich , accessed on May 9, 2017 ( PDF ).

[3] B. Radziszewski: About some derivatives of phenylacetic acid , in: Chemischeberichte , 1969 , 2 , pp. 207-210; doi : 10.1002 / cber.18690020198 .

[4] RA Aitken, MC Bibby, PA Cooper, JA Double, AL Laws, RB Ritchie, DWJ Wilson: Synthesis and Antitumour Activity of New Derivatives of Flavone-8-Acetic Acid (FAA). Part 4: Variation of the Basic Structure , in: Archiv der Pharmazie , 2000 , 333 , pp. 181–188; doi : 10.1002 / 1521-4184 (20006) 333: 6 <181 :: AID-ARDP181> 3.0.CO; 2-O .

[5] K. Ogura, N. Yahata, K. Hashizume, K. Tsuyama, K. Takahashi, H. Iida: Utilization of Methylthiomethyl p-toluyl sulfone in organic synthesis , in: Chemistry Letters , 1983 , 12 , pp. 767-770 .

[6] Lecat, M .: New binary azeotropes: 6th list in Ann. Soc. Sci. Bruxelles, Ser. B, 47 (1927) 63-71.

[Koutek-7] Hoskovec, M .; Grygarova, D .; Cvacka, J .; Streinz, L .; Zima, J .; Verevkin, SP; Koutek, B .: Determining the vapor pressures of plant volatiles from gas chromatographic retention data in J. Chrom. A 1083 (2005) 161–172, Antoine parameters by conversion from the Kirchhoff-Rankin equation.