Sinapic acid → Ethyl 3,5-dimethoxy-4-hydroxycinnamate

HRID 652956

Reaction equation

HRID 652956 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([O:15][CH3:16])[C:13]=1[OH:14])[CH:6]=[CH:7][C:8]([OH:10])=[O:9].S(=O)(=O)(O)O.[CH2:22](O)[CH3:23]>O>[CH3:16][O:15][C:12]1[CH:11]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:13]=1[OH:14])[CH:6]=[CH:7][C:8]([O:10][CH2:22][CH3:23])=[O:9]

Participants

4

Reactant 2

HCID 10743Sinapic acidHCID 73950302Sulphuric acid ethanol

Product 1

HCID 135424Ethyl 3,5-dimethoxy-4-hydroxycinnamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In an argon atmosphere, 3.00 g (13.4 mmol) of 3,5-dimethoxy-4-hydroxycinnamic acid was suspended in a sulfuric acid - ethanol (1 : 115, 50 ml) solution. The suspension was refluxed for 5.5 hours. Water was added to the reaction solution, and the mixture was extracted with methylene chloride. The organic layer was washed with an aqueous solution of sodium hydrogen carbonate and concentrated under reduced pressure to give 3.34 g (13.24 mmol) of ethyl 3,5-dimethoxy-4-hydroxycinnamate.

Workup

  1. temperatureThe suspension was refluxed for 5.5 hours
  2. extractionthe mixture was extracted with methylene chloride
  3. washThe organic layer was washed with an aqueous solution of sodium hydrogen carbonate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-44042270d45241359e930c29414b599e
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Linked notes

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