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

HRID 48146

Reaction equation

HRID 48146 reaction equation
Cl.[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[CH3:13]O>>[CH3:13][O:11][C:10](=[O:12])[CH2:9][C:6]1[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 313Hydrochloric AcidHCID 887Methanol

Product 1

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

Procedure

Hydrogen chloride was bubbled through a solution of (4-hydroxyphenyl) acetic acid (25 g, 0.16 mole) in methanol (100 ml) at room temperature. An exotherm resulted in the solution refluxing for about 10 minutes. The mixture was allowed to cool to room temperature and the solvent was evaporated in vacuo to afford methyl(4-hydroxyphenyl)acetate as a yellow oil (27.5 g) which crystallised on seeding, m.p. 46-52° C.

Workup

  1. customAn exotherm resulted in the solution
  2. temperaturerefluxing for about 10 minutes
  3. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-123330c67b6b4ba3a55b2d817c1c4a56
Source dataset
uspto-grants-2004_03
Patent number
US06703347B2

Linked notes

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