4-Coumaric acid → p-Coumaric acid ethyl ester

HRID 481262Notes

Reaction equation

HRID 481262 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[OH:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:6]=[CH:7]/[C:8]([O:10][CH2:18][CH3:19])=[O:9])=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 3224-Coumaric acidHCID 702EthanolHCID 1118Sulfuric Acid

Product 1

HCID 676946p-Coumaric acid ethyl ester

Procedure

A mixture of 10 g 4-hydroxycinnamic acid, 100 ml ethanol and 0.5 ml concentrated sulphuric acid was heated under gentle reflux for 96 hours. The reaction mixture was poured onto water, the resultant precipitate filtered off, washed with portions of water and then dried. The residue was purified by column chromatography on silica gel using ethyl acetate as eluent and recrystallisation from acetonitrile to yield 9.2 g of ethyl (E)-4-hydroxycinnamate.

Workup

  1. temperaturewas heated
  2. temperatureunder gentle reflux for 96 hours
  3. additionThe reaction mixture was poured onto water
  4. filtrationthe resultant precipitate filtered off
  5. washwashed with portions of water
  6. customdried
  7. customThe residue was purified by column chromatography on silica gel
  8. customrecrystallisation from acetonitrile

Sources & evidence

ORD record
ord-0587b9c5f5c44c65991957f22a2f1ede
Source dataset
uspto-grants-2003_11
Patent number
US06653499B1

Reaction notes

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