Water → HCID 57445724, compound

HRID 602030Notes

Reaction equation

HRID 602030 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-4c0386d8eaab47d09a50c6e030d16d69
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Reaction notes

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