Methanol → Methyl 3,5-difluoro-4-hydroxybenzoate

HRID 1675576Notes

Reaction equation

HRID 1675576 reaction equation
[CH3:1][OH:2].C([O:10][C:11]1[C:18]([F:19])=[CH:17][C:14]([C:15]#N)=[CH:13][C:12]=1[F:20])C1C=CC=CC=1.S(=O)(=O)(O)O.[OH2:26]>>[F:20][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([F:19])[C:11]=1[OH:10])[C:15]([O:2][CH3:1])=[O:26]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 574457224-Benzyloxy-3,5-difluorobenzonitrile

Product 1

HCID 53847253Methyl 3,5-difluoro-4-hydroxybenzoate

Procedure

To 100 ml of methanol were added 7.0 g of 4-benzyloxy-3,5-difluorobenzonitrile and 15 ml of concentrated sulfuric acid, and the resulting mixture was heated under reflux for 5 days. Thereafter, water was added to the reaction mixture which had been allowed to cool to near room temperature, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and 4.5 g of methyl 3,5-difluoro-4-hydroxybenzoate was obtained.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 5 days
  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-428c64bdb51c42dbbc49098738cc78d7
Source dataset
uspto-grants-2011_08
Patent number
US08003699B2

Reaction notes

Loading…