Methanol → 4-Methoxycinnamate methyl ester

HRID 464736Notes

Reaction equation

HRID 464736 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[CH3:19]O>>[CH3:19][O:10][C:9](=[O:11])[CH:8]=[CH:7][C:6]1[CH:12]=[CH:13][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 132454-Methoxy cinnamic acid

Product 1

HCID 928414-Methoxycinnamate methyl ester

Procedure

A suspension of 300 g of 4-methoxycinnamic acid (J. Chem. Soc., Chem. Comm., 355, (1978)) and 25 ml of concentrated sulfuric acid in 1.7 liters of methanol is heated to reflux for 96 hours. The solution is concentrated, cooled, and filtered to give as a white solid, 4-methoxycinnamic acid methyl ester, mp 85°-86° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 96 hours
  3. concentrationThe solution is concentrated
  4. temperaturecooled
  5. filtrationfiltered

Sources & evidence

ORD record
ord-cde8d7e643394330bc4208001dec3e3b
Source dataset
uspto-grants-1985_10
Patent number
US04548947

Reaction notes

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