Hydrochloric Acid → 2,6-Difluoro-alpha-methylbenzyl alcohol

HRID 1903830Notes

Reaction equation

HRID 1903830 reaction equation
[CH3:1][C:2]([C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[F:11])=[O:3].[BH4-].[Na+].[OH-].[Na+].Cl>C(O)(C)C.O>[F:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]([F:11])[C:4]=1[CH:2]([OH:3])[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 836431-(2,6-Difluorophenyl)ethan-1-one2×HCID 4311764Sodium borohydride

Product 1

HCID 50120752,6-Difluoro-alpha-methylbenzyl alcohol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

2,6-Difluoroacetophenone of (A) (17.2 g, 0.11 mol) is dissolved in isopropyl alcohol (50 ml) and NaBH4 (2.0 g, 0.055 mol) is added. The resultant mixture is warmed to 60° C. for about 14 hours. A solution of NaOH (4.9 g, 0.12 mol) in water (20 ml) is then added. After 1 hour at 60° C., this reaction mixture is cooled and acidified with dilute HCl. Extraction with methylene chloride provided pure title product (14.9 g, 85.5%).

Workup

  1. temperaturethis reaction mixture is cooled
  2. extractionExtraction with methylene chloride provided pure title product (14.9 g, 85.5%)

Sources & evidence

ORD record
ord-0fc9cbc4794842afbb75088d58906529
Source dataset
uspto-grants-1984_03
Patent number
US04438271

Reaction notes

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