Benzyl Alcohol → (3-Benzyloxy-4-chloro-phenyl)-acetic acid

HRID 656778Notes

Reaction equation

HRID 656778 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1F.[CH2:13]([OH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[H-].[Na+]>CN1C(=O)CCC1>[CH2:13]([O:20][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:7][C:2]=1[Cl:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 38149542-(4-Chloro-3-fluorophenyl)acetic acid

Product 1

HCID 58149177(3-Benzyloxy-4-chloro-phenyl)-acetic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

To 4-chloro-3-fluorophenylacetic acid (5 g, 26.5 mmol) and benzyl alcohol (5.5 mL, 53.0 mmol) in NMP (50 mL) at 0° C. was added sodium hydride (60% in mineral oil; 2.3 g, 58.3 mmol), and the reaction was then heated to 120° C. and stirred overnight. The mixture was acidified to pH 4 and extracted with EtOAc to give (3-benzyloxy-4-chloro-phenyl)-acetic acid.

Workup

  1. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-f925dda70f604d1fa940ad5c833c0833
Source dataset
uspto-grants-2011_12
Patent number
US08071807B2

Reaction notes

Loading…