Benzenepropanoic acid → Methyl 3-phenylpropionate

Reaction equation

[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH3:17]O>>[C:1]1([CH2:7][CH2:8][C:9]([O:11][CH3:17])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 3

HCID 107Benzenepropanoic acid

HCID 887Methanol

HCID 1118Sulfuric Acid

Product 1

HCID 7643Methyl 3-phenylpropionate

Procedure

A solution of 3-phenylpropionic acid (50 g, 0.33 mole) and conc. sulfuric acid (5 g) in methanol (220 ml) was refluxed for 1 hour with stirring, concentrated and poured into cold H2O. The mixture was extracted thrice with methylene chloride (75 ml), the organic layer was washed thrice with H2O (125 ml), dried over anhydrous MgSO4 and evaporated. The residual crude oil (54 g) was distilled under reduced pressure to give 51.5 g of methyl 3-phenylpropionate as a colorless oil having a boiling point of 94°-95° C./5 mmHg.

Workup

concentrationconcentrated
additionpoured into cold H2O
extractionThe mixture was extracted thrice with methylene chloride (75 ml)
washthe organic layer was washed thrice with H2O (125 ml)
dry with materialdried over anhydrous MgSO4
customevaporated
distillationThe residual crude oil (54 g) was distilled under reduced pressure

Sources & evidence

ORD record: ord-7856235b707843d0969564f945d077cb
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05468589

Reaction notes

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