Methanol → Methyl 3-chloro-4-hydroxyphenylacetate

HRID 1927727Notes

Reaction equation

HRID 1927727 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].OS(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-hydroxyphenylacetateYield 96%

Procedure

2-(3-Chloro-4-hydroxyphenyl)acetic acid (5.0 g, 26.8 mmol) was dissolved in 30 mL of MeOH and H2SO4 (0.744 ml, 13.4 mmol) was added dropwise at ambient temperature. The reaction was refluxed for four hours and then concentrated in vacuo. The residue was diluted with 150 mL of EtOAc and washed sequentially with saturated NaHCO3, water, and brine, dried over H2SO4, and concentrated in vacuo to provide methyl 2-(3-chloro-4-hydroxyphenyl)acetate (5.16 g, 96.0% yield) as a semi-opaque thick oil.

Workup

  1. temperatureThe reaction was refluxed for four hours
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with 150 mL of EtOAc
  4. washwashed sequentially with saturated NaHCO3, water, and brine
  5. dry with materialdried over H2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99ef8aeeb93849dcb5dddd7b453426d7
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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