Methanol → Methyl 3-chloro-4-hydroxyphenylacetate

HRID 1428742Notes

Reaction equation

HRID 1428742 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-hydroxyphenylacetateYield 99%

Procedure

To a stirred solution of 2-(3-chloro-4-hydroxyphenyl)acetic acid (3 g, 16.078 mmol) in methanol (35 mL) were added sulfuric acid (0.3 mL). The reaction mixture was refluxed for 15 h and cooled to room temperature. The solvent was evaporated. The residue dissolved in ethyl acetate and extracted with NaHCO3. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. Methyl 2-(3-chloro-4-hydroxyphenyl)acetate (3.557 g) was obtained as 99% yield.

Workup

  1. temperatureThe reaction mixture was refluxed for 15 h
  2. customThe solvent was evaporated
  3. dissolutionThe residue dissolved in ethyl acetate
  4. extractionextracted with NaHCO3
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate removed in vacuo
  8. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-73e33422780942269fd4f71af6565634
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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