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

HRID 2236372Notes

Reaction equation

HRID 2236372 reaction equation
C([O:8][C:9]1[C:16]([F:17])=[CH:15][C:12]([C:13]#N)=[CH:11][C:10]=1[F:18])C1C=CC=CC=1.S(=O)(=O)(O)O.[CH3:24][OH:25].[OH2:26]>>[F:18][C:10]1[CH:11]=[C:12]([CH:15]=[C:16]([F:17])[C:9]=1[OH:8])[C:13]([O:25][CH3:24])=[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

4-Benzyloxy-3,5-difluorobenzonitrile and 15 ml of concentrated sulfuric acid were added to 100 ml of methanol and the mixture was heated under reflux for 5 days. Then, water was added to the reaction mixture and the mixture was extracted 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 to obtain 4.5 g of methyl 3,5-difluoro-4-hydroxybenzoate represented by the formula:

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 days
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3ec56469b42346159722af4073c41f8b
Source dataset
uspto-grants-2010_05
Patent number
US07714168B2

Reaction notes

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