Methanol → Methyl 3-chloro-4-hydroxyphenylacetate

HRID 1930103Notes

Reaction equation

HRID 1930103 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 92%

Procedure

A solution of 3-chloro-4-hydroxyphenylacetic acid (24.55 g, 131.57 mmol) and sulfuric acid (0.701 mL, 13.16 mmol) in methanol (600 mL) was stirred at 75° C. for 3 hours. The reaction mixture was allowed to cool to ambient temperature evaporated to dryness and redissolved in EtOAc (500 mL), and washed with saturated brine (2×300 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford methyl 2-(3-chloro-4-hydroxyphenyl)acetate (24.20 g, 92%) as a pale yellow oil.

Workup

  1. customevaporated to dryness
  2. dissolutionredissolved in EtOAc (500 mL)
  3. washwashed with saturated brine (2×300 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-a889c15de3c54d00a97b360ffc2a44dd
Source dataset
uspto-grants-2012_05
Patent number
US08188092B2

Reaction notes

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