Methanol → Methyl p-coumarate

HRID 2308125Notes

Reaction equation

HRID 2308125 reaction equation
[CH:1]1[C:6](/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10])=[CH:5][CH:4]=[C:3]([OH:12])[CH:2]=1.S(=O)(=O)(O)O.[CH3:18]O>>[CH3:18][O:10][C:9](=[O:11])[CH:8]=[CH:7][C:6]1[CH:5]=[CH:4][C:3]([OH:12])=[CH:2][CH:1]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 637542P-Coumaric Acid

Product 1

HCID 92203Methyl p-coumarate

Procedure

51.2 g (312 mmol) of p-coumaric acid were dissolved in 330 ml of methanol and treated with 10 ml of concentrated sulphuric acid. The solution was heated under reflux for 2 hours. Subsequently the majority of the methanol (about 200 ml) was distilled off and the residue remaining behind was poured into 1.31 of ice-water. The separated ester was filtered off under suction and washed in succession with cold water, with a small amount of cold NaHCO3 solution and again with cold water. Drying at 50° C. in a water-jet vacuum gave 51.1 g of 3-(4-hydroxyphenyl)acrylic acid methyl ester in the form of a light brownish coloured powder.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 2 hours
  3. distillationSubsequently the majority of the methanol (about 200 ml) was distilled off
  4. additionwas poured into 1.31 of ice-water
  5. filtrationThe separated ester was filtered off under suction
  6. washwashed in succession with cold water, with a small amount of cold NaHCO3 solution and again with cold water
  7. dry with materialDrying at 50° C. in a water-jet vacuum

Sources & evidence

ORD record
ord-ad2d7361e42a47a8813663ee8602aaa0
Source dataset
uspto-grants-2004_12
Patent number
US06833421B1

Reaction notes

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