Dopac → Methyl 3,4-dihydroxyphenylacetate

HRID 582047

Reaction equation

HRID 582047 reaction equation
[OH: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>>[OH: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 547DopacHCID 887MethanolHCID 1118Sulfuric Acid

Product 1

HCID 11008556Methyl 3,4-dihydroxyphenylacetate

Procedure

A mixture of 3,4-dihydroxyphenylacetic acid (10.0 g) and concentrated sulphuric acid (0.5 ml ) in methanol (70 ml) was heated under reflux for 16 hours. The mixture was concentrated, water was added and the mixture was neutralised to pH7 using sodium carbonate. The cloudy solution obtained was extracted with dichloromethane (200 ml), dried (Na2SO4) and evaporated to give a yellow gum (7.64 g). LRMS m/z=183(m+1)+.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. concentrationThe mixture was concentrated
  4. additionwater was added
  5. customThe cloudy solution obtained
  6. extractionwas extracted with dichloromethane (200 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-eccd76d2b243402faaa07ef69d3c5c89
Source dataset
uspto-grants-1999_07
Patent number
US05922747

Linked notes

Loading…