Benzyl Alcohol → Benzyl Alcohol

HRID 885296Notes

Reaction equation

HRID 885296 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[F:11][C:12]1[CH:13]=[C:14]([CH2:19][C:20]([OH:22])=[O:21])[CH:15]=[C:16](F)[CH:17]=1>CN1C(=O)CCC1>[CH2:1]([O:8][C:16]1[CH:15]=[C:14]([CH2:19][C:20]([OH:22])=[O:21])[CH:13]=[C:12]([F:11])[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 1454243,5-Difluorophenylacetic acid

Product 2

HCID 244Benzyl AlcoholYield 30%HCID 58149022HCID 58149022, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To benzyl alcohol (1.4 g, 12.8 mmol) in NMP (30 mL) was added sodium hydride (60% in mineral oil; 0.5 g, 12.8 mmol), and the mixture was stirred for 20 minutes. 3,5-Difluorophenylacetic acid (1.0 g, 5.8 mmol) was added, and the reaction was stirred at 100° C. for 2 hours, and then 60° C. overnight. The mixture was worked-up to give the desired product, plus ˜30% of benzyl alcohol impurity (2.0 g).

Workup

  1. stirringthe reaction was stirred at 100° C. for 2 hours
  2. custom60° C. overnight

Sources & evidence

ORD record
ord-b9de998cbde24023880e5522f5180e55
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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