Sodium Hydroxide → (2-Fluoro-3,4-dimethoxyphenyl)methanol

HRID 274490Notes

Reaction equation

HRID 274490 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[C:7]=1[F:16])(=O)C.[OH-].[Na+]>CO>[F:16][C:7]1[C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=[CH:11][C:6]=1[CH2:5][OH:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 536894592-Fluoro-3,4-dimethoxybenzyl acetate

Product 1

HCID 19838191(2-Fluoro-3,4-dimethoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.4 g of 2-fluoro-3,4-dimethoxybenzyl acetate are heated to 80° for 1.5 hours together with 50 ml of methanol and 50 ml of 1N sodium hydroxide solution. After evaporation of the methanol the residue is extracted with methylene chloride. The combined extracts are washed with water, dried over sodium sulfate and evaporated. The residue is chromatographed on 80 g of silica gel with methylene chloride/methanol (95:5). 2-fluoro-3,4-dimethoxybenzyl alcohol is obtained as an oil.

Workup

  1. customAfter evaporation of the methanol the residue
  2. extractionis extracted with methylene chloride
  3. washThe combined extracts are washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue is chromatographed on 80 g of silica gel with methylene chloride/methanol (95:5)

Sources & evidence

ORD record
ord-12b7507858e34a4a9ff0c2ddf6ecfa27
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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