BENZYL GLYCOLATE

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CAS:30379-58-9
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  • 2025-04-04
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  • 2024-07-25
  • CAS:30379-58-9
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BENZYL GLYCOLATE Basic information
Product Name:BENZYL GLYCOLATE
Synonyms:BENZYL GLYCOLATE;Benzyl 2-hydroxyacetate;Acetic acid, hydroxy-, phenylMethyl ester;Benzyl glycolate 97%;Acetic acid, 2-hydroxy-, phenylmethyl ester;Ethanol,6-(propylamino)-;Phenylmethyl 2-hydroxyacetate;Phenylmethyl glycolate
CAS:30379-58-9
MF:C9H10O3
MW:166.17
EINECS:
Product Categories:Esters;C8 to C9;Carbonyl Compounds
Mol File:30379-58-9.mol
BENZYL GLYCOLATE Structure
BENZYL GLYCOLATE Chemical Properties
Boiling point 136 °C/14 mmHg (lit.)
density 1.171 g/mL at 25 °C (lit.)
refractive index n20/D 1.527(lit.)
Fp >230 °F
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Sparingly), Methanol (Slightly)
pka12.96±0.10(Predicted)
form Oil
color Colourless
InChIInChI=1S/C9H10O3/c10-6-9(11)12-7-8-4-2-1-3-5-8/h1-5,10H,6-7H2
InChIKeyVPYJBEIOKFRWQZ-UHFFFAOYSA-N
SMILESC(OCC1=CC=CC=C1)(=O)CO
Safety Information
WGK Germany 3
HS Code 2918199890
Storage Class10 - Combustible liquids
MSDS Information
ProviderLanguage
SigmaAldrich English
BENZYL GLYCOLATE Usage And Synthesis
UsesBenzyl Glycolate was utilized as a potential moiety for the preparation of phosphonate dipeptides as potential inhibitors of VanX.
UsesBenzyl glycolate may be used for the synthesis of the methyl [2-(2′-benzyloxy-2′-oxoethyl)-5-acetamido-4,7,8,9- tetra-O-acetyl-3,5-dideoxy-α- and -β-D-glycero-D-galacto-2-nonulopyranosid]onate. It may be used for the preparation of monosaccharide building blocks. It may also be used for the synthesis of the following new polymeric phosphazenes having pendent esters of glycolic or lactic acid as side units:
  • poly[bis(ethyl glycolato)phosphazene]
  • poly[bis(ethyl lactato)phosphazene]
  • poly[bis(benzyl glycolato)phosphazene]
  • poly[bis(benzyl lactato)phosphazene]
General DescriptionBenzyl glycolate is a benzyl ester of glycolic acid.
Synthesis
Glycolic acid

79-14-1

Benzyl bromide

100-39-0

BENZYL GLYCOLATE

30379-58-9

The general procedure for the synthesis of phenylmethyl ethanoate from ethanoic acid and benzyl bromide was as follows: first, a suspension formed by 2-hydroxyacetic acid (70% aqueous solution, 889 mg, 12.0 mmol) and Cs2CO3 (1955 mg, 6.00 mmol) in a solvent mixture of methanol (22 mL) and water (4 mL) was stirred for 30 min at room temperature. Subsequently, the solvent was removed and the residue was dissolved in DMF (18 mL) pre-cooled to 0 °C. After 10 min, benzyl bromide (2155 mg, 12.6 mmol) was added and the reaction mixture was continued to be stirred for 24 h at room temperature. Upon completion of the reaction, the reaction was quenched with brine (20 mL) and the organic layer was extracted with ethyl acetate (3 x 25 mL). The extract was washed sequentially with water (25 mL) and brine (20 mL), dried over MgSO4 and concentrated in vacuum to afford 1877 mg (97% yield) of benzyl 2-hydroxyacetate as a colorless liquid.HPLC analysis showed a retention time of 2.68 min (70%).

References[1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 16, p. 4903 - 4909
[2] Journal of Organic Chemistry, 2000, vol. 65, # 22, p. 7667 - 7675
[3] Patent: US2016/340365, 2016, A1. Location in patent: Paragraph 0126; 0127
[4] Patent: US2016/297784, 2016, A1. Location in patent: Paragraph 0150; 0151
[5] Journal of the American Chemical Society, 2010, vol. 132, # 31, p. 10920 - 10934
BENZYL GLYCOLATE Preparation Products And Raw materials
Raw materialsGlycolic acid-->Benzyl alcohol-->Benzyl bromide-->Cesium carbonate-->Water-->Methanol
Preparation Productsbenzyl 2-(difluoromethoxy)acetate
Tag:BENZYL GLYCOLATE(30379-58-9) Related Product Information
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