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

HRID 1088855Notes

Reaction equation

HRID 1088855 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:12][CH3:13])=[C:5](C=C(Cl)C=1)C=O.[C:14]([O:19]CC)(=[O:18])/[CH:15]=[CH:16]/[CH3:17].[CH3:22][C:23]([CH3:26])([O-])[CH3:24].[K+].[ClH:28]>CN1CCCC1=O>[CH3:1][O:2][C:3]1[CH:22]=[C:23]([CH:26]=[CH:17][CH:16]=[CH:15][C:14]([OH:19])=[O:18])[CH:24]=[C:5]([Cl:28])[C:4]=1[O:12][CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 429065Ethyl trans-crotonateHCID 41722755-Chloro-2,3-dimethoxybenzaldehydeHCID 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 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-e6263416a201468591420a2156fdb527
Source dataset
uspto-grants-1990_10
Patent number
US04963590

Reaction notes

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