Hydrochloric Acid → Cinnamic acid, p-hydroxy-, acetate

HRID 1953359Notes

Reaction equation

HRID 1953359 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.N1C=CC=CC=1.[C:19](Cl)(=[O:21])[CH3:20].Cl>C1COCC1>[C:19]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:11][CH:12]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3224-Coumaric acidHCID 1049PyridineHCID 6367Acetyl chloride

Product 1

HCID 85857Cinnamic acid, p-hydroxy-, acetateYield 63.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 16.5 g (0.101 mol) of 4-hydroxycinnamic acid and 200 ml of a THF solution of 24 ml (0.297 mol) of pyridine was dropwise added 20 ml (0.281 mol) of acetyl chloride over 1 hour at room temperature. After the resulting mixture was stirred at room temperature for 7 hours, the reaction system was poured into 300 ml of a 2N aqueous solution of hydrochloric acid. After extracting with ether and concentrating the organic phase, there was obtained 13.14 g (0.064 mol) of 4-acetoxycinnamic acid as a white solid. The yield was 63%.

Workup

  1. customover 1 hour
  2. customat room temperature
  3. extractionAfter extracting with ether
  4. concentrationconcentrating the organic phase

Sources & evidence

ORD record
ord-66b47beff345493eac167cf2bc43bbad
Source dataset
uspto-grants-2000_09
Patent number
US06117359

Reaction notes

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