2-(4-Acetoxyphenoxy)propanoic acid → 2-(4-Hydroxy-phenoxy)-propionic acid

HRID 1165347Notes

Reaction equation

HRID 1165347 reaction equation
C([O:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][CH:10]([CH3:14])[C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)(=O)C>Cl.C(O)C>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH:10]([CH3:14])[C:11]([OH:13])=[O:12])=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 147448922-(4-Acetoxyphenoxy)propanoic acid

Product 1

HCID 1011822-(4-Hydroxy-phenoxy)-propionic acidYield 93.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

2-(4-Acetoxyphenoxy)propanoic acid (1.2 g, 5.3 mmol) is hydrolyzed by refluxing ethanol (15 mL) and 2 drops of concentrated hydrochloric acid (36%) for 2 hours. Ethanol is removed under reduced pressure to give 2-(4-hydroxyphenoxy)propanoic acid (0.9 g yield 93%): m.p. 136°-137.5° C., IR (KBr) 3265 (vs), 1707 (vs); 1H NMR (acetone-d6) delta 1.52 (d, J=6.8 Hz, 3H), 4.67 (q, J=6.8 Hz, 1H), 6.75 (M, 4H).

Workup

  1. customEthanol is removed under reduced pressure

Sources & evidence

ORD record
ord-09997791ea8142da837c547717b7a612
Source dataset
uspto-grants-1990_03
Patent number
US04908476

Reaction notes

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