Potassium Bicarbonate → (4-Fluoro-2-methoxyphenyl)methanol

HRID 1838746Notes

Reaction equation

HRID 1838746 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1.[BH4-].[Na+].C(=O)([O-])O.[K+]>CO.O>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

6

Reactant 3

HCID 516893Potassium BicarbonateHCID 27745374-Fluoro-2-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 17750770(4-Fluoro-2-methoxyphenyl)methanolYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

An ice-cold solution of 5.6 g of 4-fluoro-2-methoxy-benzaldehyde in 75 ml of methanol was treated portionwise (5 portions within 50 minutes) with 1.51 g (40mmol) of sodium borohydride and the reaction mixture was stirred for another 1 hour at room temperature. A dispersion of 7 g of potassium hydrogencarbonate in 20 ml of water was added and the mixture stirred for 30 minutes at room temperature. Thereupon, most of the methanol was evaporated under reduced pressure and the residue extracted with dichloromethane. The organic phase was separated, dried and concentrated under reduced pressure to yield 5.15 g (91% of theory) of (4-fluoro-2-methoxy-phenyl)-methanol as a white solid; MS: 156 (M)+.

Workup

  1. stirringthe mixture stirred for 30 minutes at room temperature
  2. customThereupon, most of the methanol was evaporated under reduced pressure
  3. extractionthe residue extracted with dichloromethane
  4. customThe organic phase was separated
  5. customdried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2cb5f5fa011b4345916cf73111b70c4c
Source dataset
uspto-grants-2004_01
Patent number
US06673931B2

Reaction notes

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