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

HRID 1195951Notes

Reaction equation

HRID 1195951 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 stirred for 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. stirringThe solution was stirred for 0.5 h more at 20° C.
  3. additionthe solution was poured
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washwas washed with water
  7. extractionextracted
  8. customthe semisolid product was separated
  9. washwashed with water

Sources & evidence

ORD record
ord-0367d9c554c744308c9c1d7987e99c5c
Source dataset
uspto-grants-1992_05
Patent number
US05112861

Reaction notes

Loading…