Hydrochloric Acid → 5-(3,4-Dimethoxy-5-chlorophenyl)-2,4-pentadienoic acid

HRID 1757637Notes

Reaction equation

HRID 1757637 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([Cl:13])[C:10]=1[O:11][CH3:12])[CH:6]=O.[C:14]([O:19]CC)(=[O:18])/[CH:15]=[CH:16]/[CH3:17].CC(C)([O-])C.[K+].Cl>CN1CCCC1=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:17][CH:16]=[CH:15][C:14]([OH:19])=[O:18])[CH:8]=[C:9]([Cl:13])[C:10]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2400523-Chloro-4,5-dimethoxybenzaldehydeHCID 429065Ethyl trans-crotonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 542197795-(3,4-Dimethoxy-5-chlorophenyl)-2,4-pentadienoic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution containing 10.0 g of 3,4-dimethoxy-5-chlorobenzaldehyde and 8.3 ml of ethyl crotonate in 65 ml of N-methylpyrrolidone 6.7 g of potassium tert.-butoxide was added with stirring. The solution was stirredfor 0.5 h more at 20° C. and the solution was poured then to a mixture of ice and hydrochloric acid and extracted with ether. The ether extract was washed with water and extracted then with NaHCO3 -solution. The aqueous phase was acidified with hydrochloric acid and the semisolid product was separated and washed with water. Yield 7.3 g (55%).

Workup

  1. additionwas added
  2. additionthe solution was poured
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with water
  6. extractionextracted
  7. customthe semisolid product was separated
  8. washwashed with water

Sources & evidence

ORD record
ord-06d6099d09284a53a831c593b8624073
Source dataset
uspto-grants-1995_08
Patent number
US05446194

Reaction notes

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