Hydroxyphenylacetic acid → Benzeneacetic acid, 4-hydroxy-, methyl ester

HRID 1579044Notes

Reaction equation

HRID 1579044 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:17]O>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:17])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 887MethanolHCID 1118Sulfuric Acid

Product 1

HCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Procedure

A mixture of 37 g. of 4-hydroxyphenylacetic acid, 370 ml. of methanol and 0.1 ml. of sulfuric acid is refluxed for 6 hours, cooled, poured into ice water, and extracted with methylene chloride. The organic extract is washed with water to neutrality, dried over sodium sulfate and evaporated to dryness under vacuo, to yield methyl 4-hydroxyphenylacetate.

Workup

  1. additionA mixture of 37 g
  2. temperaturecooled
  3. extractionextracted with methylene chloride
  4. extractionThe organic extract
  5. washis washed with water to neutrality
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness under vacuo

Sources & evidence

ORD record
ord-a18451c2737d4ad68aa619f07f65c6e5
Source dataset
uspto-grants-1976_02
Patent number
US03940407

Reaction notes

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