Methanol → Methyl 3-chloro-4-hydroxyphenylacetate

HRID 1930187Notes

Reaction equation

HRID 1930187 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].S(=O)(=O)(O)O.[CH3:18]O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:18])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

4

Reactant 3

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

Product 1

HCID 92625Methyl 3-chloro-4-hydroxyphenylacetate

Conditions

Temperature
25 °C

Procedure

A solution of 2-(3-chloro-4-hydroxyphenyl)acetic acid (1000 g, 5359 mmol) and sulfuric acid (0.029 L, 535 mmol) in methanol (10 L) was stirred at reflux for 3 hours. The reaction mixture was cooled to 25° C. The solvent was then removed in vacuo. Ethyl acetate (5.0 L) was added and the solution was washed with water (4.0 L), brine (2.0 L), dried (magnesium sulphate), filtered and the solvent was removed in vacuo. Gave methyl 2-(3-chloro-4-hydroxyphenyl)acetate (1078 g, 99%) as an orange oil.

Workup

  1. temperatureat reflux for 3 hours
  2. customThe solvent was then removed in vacuo
  3. additionEthyl acetate (5.0 L) was added
  4. washthe solution was washed with water (4.0 L), brine (2.0 L)
  5. dry with materialdried (magnesium sulphate)
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-46e9f10832084a8cb61316ca7a423c3a
Source dataset
uspto-grants-2012_05
Patent number
US08188092B2

Reaction notes

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