Methyl 2-(4-acetoxyphenoxy)propanoate → Propanoic acid, 2-(4-hydroxyphenoxy)-, methyl ester
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]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
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
- concentrationconcentrated HCL (36%, 2 drops)