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

HRID 341714Notes

Reaction equation

HRID 341714 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.Cl.[CH2:13](N(CC)CC)C>CO>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 313Hydrochloric AcidHCID 8471Triethylamine

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Hydroxyphenylacetic acid (1.75 g) was dissolved in methanol (30 ml) and 10M aqueous hydrochloric acid (0.15 ml) was added and heated to reflux for 15 hours. After cooling to room temperature, triethylamine (1 ml) was added, the mixture concentrated, purified by flash chromatography using silica gel (30 g) and eluted with ethyl acetate-hexane (2:8 volume by volume) to give Methyl 4-Hydroxyphenylacetate (4) (1.693 g). This was confirmed by spectroscopy--1H NMR (CDCl3) δ 3.58 (s, 2 H), 3.73 (s, 3 H), 6.75 (d, 2 H), 7.10 (d, 2 H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 15 hours
  3. concentrationthe mixture concentrated
  4. custompurified by flash chromatography
  5. washeluted with ethyl acetate-hexane (2:8 volume by volume)

Sources & evidence

ORD record
ord-6508b97eda74498abe5d412401751a6c
Source dataset
uspto-grants-1999_01
Patent number
US05855885

Reaction notes

Loading…