Benzyl Alcohol → (3-Benzyloxy-5-trifluoromethyl-phenyl)-acetic acid

HRID 563549Notes

Reaction equation

HRID 563549 reaction equation
F[C:2]1[CH:3]=[C:4]([CH2:12][C:13]([OH:15])=[O:14])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH2:16]([OH:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[H-].[Na+]>CN1C(=O)CCC1>[CH2:16]([O:23][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([OH:15])=[O:14])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 27591723-Fluoro-5-(trifluoromethyl)phenylacetic acid

Product 1

HCID 59644613(3-Benzyloxy-5-trifluoromethyl-phenyl)-acetic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

To 3-fluoro-5-(trifluoromethyl)phenylacetic acid (2.0 g, 9.0 mmol) and benzyl alcohol (1.9 mL, 18.0 mmol) in NMP (10 mL) was added sodium hydride (60% in mineral oil; 0.8 g, 19.8 mmol), and the reaction was stirred at 120° C. for 3 hours. The mixture was acidified and extracted with EtOAc, and the crude material was purified by silica gel chromatography to give the title compound.

Workup

  1. extractionextracted with EtOAc
  2. customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-429b6ce40a85418c86226b0a2f758d7a
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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