Potassium Hydroxide → 4-Fluoro-2,3-dimethoxybenzene butanoic acid

HRID 979806Notes

Reaction equation

HRID 979806 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH:11]=[O:12])=[C:4]([O:13][CH3:14])[C:3]=1[O:15][CH3:16].[OH-:17].[K+]>O.C(O)C.[Ag]=O.[N+]([O-])([O-])=O.[Ag+]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:17])=[O:12])=[C:4]([O:13][CH3:14])[C:3]=1[O:15][CH3:16]

Participants

7

Reactant 2

HCID 14797Potassium HydroxideHCID 571383154-Fluoro-2,3-dimethoxybenzene butanal

Product 1

HCID 867411834-Fluoro-2,3-dimethoxybenzene butanoic acidYield 30%

Reagents, catalysts & solvents 4

HCID 24470Silver NitrateCatalystHCID 92152Silver(II) oxideCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

The product from Example 55 (12.6 g) was oxidized with silver oxide prepared in situ from a solution of silver nitrate (15.6 g) in H2O (22 ml) and potassium hydroxide (12.7 g) in H2O (22 ml). The reaction was done in ethanol (170 ml) with stirring at room temperature. After 1 hour, the precipitated silver salts were filtered, washed with water and concentrated to 1/2 volume. The aqueous basic layer was diluted with water extracted with hexane several times, acidified and extracted with ethyl acetate. The organic layer was separated, dried and evaporated to afford the desired acid in 30% yield.

Workup

  1. filtrationthe precipitated silver salts were filtered
  2. washwashed with water
  3. concentrationconcentrated to 1/2 volume
  4. additionThe aqueous basic layer was diluted with water
  5. extractionextracted with hexane several times
  6. extractionextracted with ethyl acetate
  7. customThe organic layer was separated
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-7a71f5c47a55487b85dc01e91df675b1
Source dataset
uspto-grants-1987_01
Patent number
US04634705

Reaction notes

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