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

HRID 2254761Notes

Reaction equation

HRID 2254761 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-4e46a2d0c3894bcf9f7c0a647def9bdb
Source dataset
uspto-grants-1993_08
Patent number
US05236952

Reaction notes

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