Water → HCID 57445724, compound

HRID 1675584Notes

Reaction equation

HRID 1675584 reaction equation
[OH2:1].[Mn]([O-])(=O)(=O)=O.[K+].[CH2:8]([O:15][C:16]1[C:23]([O:24][CH3:25])=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][C:17]=1[F:26])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CC(C)=O>[CH2:8]([O:15][C:16]1[C:23]([O:24][CH3:25])=[CH:22][C:19]([C:20]([OH:1])=[O:21])=[CH:18][C:17]=1[F:26])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 561417HCID 561417, compound

Product 1

HCID 57445724HCID 57445724, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 200 ml of water and 6.8 g of potassium permanganate was added dropwise 7.5 g of 4-benzyloxy-3-fluoro-5-methoxybenzaldehyde dissolved in 200 ml of acetone at 15 to 20° C., and the resulting mixture was stirred at room temperature for 3 days. Thereafter, the reaction mixture was concentrated under reduced pressure to about half volume. To the concentrated solution were added an aqueous sodium hydrogen sulfite solution and dilute hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure, and 4-benzyloxy-3-fluoro-5-methoxybenzoic acid was obtained.

Workup

  1. concentrationThereafter, the reaction mixture was concentrated under reduced pressure to about half volume
  2. additionTo the concentrated solution were added an aqueous sodium hydrogen sulfite solution and dilute hydrochloric acid
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bf098991c3fe4d6999c47a8f854d9c5c
Source dataset
uspto-grants-2011_08
Patent number
US08003699B2

Reaction notes

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