Methanol → Methyl p-coumarate

HRID 1249951Notes

Reaction equation

HRID 1249951 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>>[OH:12][C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[CH:8][C:9]([O:11][CH3:18])=[O:10])=[CH:1][CH:2]=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 1.3 l 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 methyl 3-(4-hydroxyphenyl)-acrylate 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 1.3 l 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-0f1a72c90fcc4c06aafeb6027e124046
Source dataset
uspto-grants-2002_01
Patent number
US06335409B1

Reaction notes

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