Methanol → 4-Methoxycinnamate methyl ester

HRID 1380947Notes

Reaction equation

HRID 1380947 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-d7281767d2a442e89f77e63b36599aeb
Source dataset
uspto-grants-1986_04
Patent number
US04584313

Reaction notes

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