Methanol → Methyl 3-chloro-4-hydroxyphenylacetate

HRID 1728843Notes

Reaction equation

HRID 1728843 reaction equation
[Cl: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]([Cl:1])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1185343-Chloro-4-hydroxyphenylacetic acid

Product 1

HCID 92625Methyl 3-chloro-4-hydroxyphenylacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 50 g of 3-chloro-4-hydroxybenzeneacetic acid, 250 ml of methyl alcohol and 10 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 saturated sodium bicarbonate and saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel:30% ethyl acetate/hexane) to give 49.9 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 saturated sodium bicarbonate and saturated sodium chloride
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by column chromatography (silica gel:30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2a3ffd869b024957b3d1cc09bf278ec5
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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