Methyl 2-(4-acetoxyphenoxy)propanoate → Propanoic acid, 2-(4-hydroxyphenoxy)-, methyl ester

HRID 1085335Notes

Reaction equation

HRID 1085335 reaction equation
C([O:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1)(=O)C>CO>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[CH:16][CH:17]=1

Participants

3

Reactant 1

HCID 20062087Methyl 2-(4-acetoxyphenoxy)propanoate

Product 1

HCID 366926Propanoic acid, 2-(4-hydroxyphenoxy)-, methyl esterYield 98.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(4-acetoxyphenoxy)propanoate (1.0 g, 4.2 mmol) is hydrolyzed by refluxing for 2 hours at 80° C. with methanol (10 mL) and concentrated HCL (36%, 2 drops). The reaction product is concentrated under reduced pressure to obtain methyl 2-(4-hydroxyphenoxy)propanoate (0.81 g). Conversion 99%, selectivity 99%, yield 97%; IR (neat) 1757 (vs) 1H NMR (CDC13) delta 1.60 (d, J=7.0 Hz, 3H), 3.80 (s, 3H), 4.85 (q, J=7.0 Hz, 1H), 6.82 (s, 4H).

Workup

  1. concentrationconcentrated HCL (36%, 2 drops)
  2. concentrationThe reaction product is concentrated under reduced pressure

Sources & evidence

ORD record
ord-b4dde146b87a4313943855c28d432f68
Source dataset
uspto-grants-1991_04
Patent number
US05008439

Reaction notes

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