Benzyl Alcohol → (5-Benzyloxy-2-chloro-phenyl)-acetic acid

HRID 885285Notes

Reaction equation

HRID 885285 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Cl:11][C:12]1[CH:17]=[CH:16][C:15](F)=[CH:14][C:13]=1[CH2:19][C:20]([OH:22])=[O:21]>CN1C(=O)CCC1>[CH2:1]([O:8][C:15]1[CH:16]=[CH:17][C:12]([Cl:11])=[C:13]([CH2:19][C:20]([OH:22])=[O:21])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 35354302-(2-Chloro-5-fluorophenyl)acetic acid

Product 1

HCID 58149280(5-Benzyloxy-2-chloro-phenyl)-acetic acidYield 144.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To benzyl alcohol (1.1 g, 10 mmol) in NMP (20 mL) was added sodium hydride (60% in mineral oil; 0.44 g, 11 mmol), and the mixture was stirred for 30 minutes at room temperature. The mixture was then added to a vial containing 2-chloro-5-fluorophenylacetic acid (1 g, 4.5 mmol), and the reaction was stirred at 120° C. for 3 hours. Acidic work-up gave the desired product (1.8 g).

Workup

  1. additionThe mixture was then added to
  2. stirringthe reaction was stirred at 120° C. for 3 hours

Sources & evidence

ORD record
ord-a6b229c617f4494bba6d916ec2c70f72
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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