Methanol → Methyl 2-(3-fluoro-4-hydroxyphenyl)acetate

HRID 1728842Notes

Reaction equation

HRID 1728842 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[CH3:13]O.S(=O)(=O)(O)O>O>[CH3:13][O:11][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 680143-Fluoro-4-hydroxybenzeneacetic acid

Product 1

HCID 10797559Methyl 2-(3-fluoro-4-hydroxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.0 g of 3-fluoro-4-hydroxybenzeneacetic acid, 10 ml of methyl alcohol and 1 ml of concentrated sulfuric acid is heated at reflux temperature for 23.5 hours. The cooled solution is diluted with water and extracted with methylene chloride. The organic layer is washed with water, saturated sodium bicarbonate, water and saturated sodium chloride; dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel:25% ethyl acetate/hexane) to give 1.9 g of the desired product.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 23.5 hours
  3. extractionextracted with methylene chloride
  4. washThe organic layer is washed with water, saturated sodium bicarbonate, water and saturated sodium chloride
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by column chromatography (silica gel:25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-dadab631b8b74d28ba658be474fa4496
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

Loading…