Benzenepropanoic acid → Methyl 3-phenylpropionate

HRID 867787Notes

Reaction equation

HRID 867787 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.[N+](=[CH2:14])=[N-]>CCOCC>[C:1]1([CH2:7][CH2:8][C:9]([O:11][CH3:14])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 107Benzenepropanoic acidHCID 9550Diazomethane

Product 1

HCID 7643Methyl 3-phenylpropionateYield 83.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To an ice-cooled and stirred solution of 3-phenylpropionic acid (8.0 g, 0.053 mol) in 30 ml of ether was slowly added an excess solution of diazomethane in ether. After concentration of ether, the residue was distilled under reduced pressure to give a colorless transparent oil of methyl 3-phenylpropionate (7.25 g, 0.044 mol, yield 83.1%, b.p. 106°-108° C./10 mmHg), which was assigned the structure by the following data:

Workup

  1. distillationAfter concentration of ether, the residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-ef22f6135a874911b2596c16fef175d8
Source dataset
uspto-grants-1988_10
Patent number
US04775692

Reaction notes

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