Acetone → (3-Bromo-4-methoxyphenyl)methanol

HRID 1662748Notes

Reaction equation

HRID 1662748 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[BH4-].[Na+].CC(C)=O>CO.C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

6

Reactant 3

HCID 180AcetoneHCID 986623-Bromo-4-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 13551346(3-Bromo-4-methoxyphenyl)methanolYield 98.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of 100 g of 3-bromo-para-anisaldehyde in MeOH (700 ml) and THF (100 ml), on ice, was added 7.50 g of NaBH4. After the solution was warmed to room temperature and stirred for two hours, acetone was added. The reaction solution was concentrated under reduced pressure, water and EtOAc were added to the residue, and liquid separation was performed. The organic layer was washed with saturated brine and dried over MgSO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc/n-hexane=1/1; v/v) to obtain 99.8 g of the title compound (colorless solid).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, water and EtOAc
  2. additionwere added to the residue, and liquid separation
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over MgSO4
  5. customthe drying agent was separated by filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc/n-hexane=1/1; v/v)

Sources & evidence

ORD record
ord-ca6f90c1034b4fd183e50950f12e51a7
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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