Water → HCID 57445724, compound

HRID 2236382Notes

Reaction equation

HRID 2236382 reaction equation
[CH2:1]([O:8][C:9]1[C:16]([O:17][CH3:18])=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[F:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[Mn]([O-])(=O)(=O)=[O:22].[K+]>CC(C)=O>[CH2:1]([O:8][C:9]1[C:16]([O:17][CH3:18])=[CH:15][C:12]([C:13]([OH:22])=[O:14])=[CH:11][C:10]=1[F:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=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

A solution of 7.5 g of 4-benzyloxy-3-fluoro-5-methoxybenzaldehyde in 200 ml of acetone was added dropwise at 15 to 20° C. to a mixture of 200 ml of water and 6.8 g of potassium permanganate. The mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated to about a half amount under reduced pressure. Aqueous sodium hydrogen sulfite solution and dilute hydrochloric acid were added to the concentrate and extracted twice with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to obtain 4-benzyloxy-3-fluoro-5-methoxybenzoic acid.

Workup

  1. concentrationThe reaction mixture was concentrated to about a half amount under reduced pressure
  2. additionAqueous sodium hydrogen sulfite solution and dilute hydrochloric acid were added to the
  3. concentrationconcentrate
  4. extractionextracted twice with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-662db748eb7f4e16a7529883286b92bf
Source dataset
uspto-grants-2010_05
Patent number
US07714168B2

Reaction notes

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