Methyl Acrylate → HCID 53829730, compound

HRID 1076318Notes

Reaction equation

HRID 1076318 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=[O:28])[CH:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:12][CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:4][CH:3]=1.[C:29]([O:33]C)(=[O:32])[CH:30]=[CH2:31]>CO.C(COC)OC>[CH3:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH:14]=[CH:13][CH2:12][C:11]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:10](=[O:28])[CH:9]=[CH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:31][CH2:30][C:29]([OH:33])=[O:32]

Participants

5

Reactant 2

HCID 7294Methyl AcrylateHCID 53744667HCID 53744667, compound

Product 1

HCID 53829730HCID 53829730, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Triton B (1 ml., 40% in MeOH) is added to a stirred soluton of 1-(p-chlorophenyl)-4-phenyl-7-(o-methylphenyl)-1,6-heptadien-3-one (15.47 g., 0.04 mole) in glyme (150 ml.), followed by addition of methyl acrylate (4.13 g., 0.048 mole) in glyme (25 ml.). After stirring for 24 hours, the solvent is removed in vacuo, and water (600 ml.) and dilute hydrochloric acid (25 ml.) are added to the residue. The organic material is extracted into ether and these extracts are washed with water, saturated brine and dried (Na2SO4). After removal of the solvent, the residue is heated on a steam bath with a solution of 20% sodium hydroxide (25 ml.) in methanol (300 ml.) for 20 hours. The methanol is removed in vacuo and the residue is dissolved in water (1200 ml.). Extraction with ether removes unreacted ketone. Ether is expelled from the aqueous phase by warming. The solution is cooled in an ice bath, acidified with dilute hydrochloric acid (30 ml.), and the yellowish solid that precipitates is filtered and air-dried; yield 12.85 g., m.p. 60°-80°C. (glass). Several recrystallizations from n-butyl chloride, followed by a final recrystallization and ethanol gives material with m.p. 163.5°-165°C. Anal. Calcd. for C29H27ClO3 : C, 75.89; H, 5.93; Found: C, 75.67; H, 5.76.

Workup

  1. customthe solvent is removed in vacuo, and water (600 ml.) and dilute hydrochloric acid (25 ml.)
  2. additionare added to the residue
  3. extractionThe organic material is extracted into ether
  4. washthese extracts are washed with water, saturated brine
  5. dry with materialdried (Na2SO4)
  6. customAfter removal of the solvent
  7. temperaturethe residue is heated on a steam bath with a solution of 20% sodium hydroxide (25 ml.) in methanol (300 ml.) for 20 hours
  8. customThe methanol is removed in vacuo
  9. dissolutionthe residue is dissolved in water (1200 ml.)
  10. extractionExtraction with ether
  11. customremoves unreacted ketone
  12. temperatureby warming
  13. temperatureThe solution is cooled in an ice bath
  14. filtrationthe yellowish solid that precipitates is filtered
  15. customair-dried
  16. customSeveral recrystallizations from n-butyl chloride
  17. customrecrystallization and ethanol
  18. customgives material with m.p. 163.5°-165°C

Sources & evidence

ORD record
ord-2070897c958347dfb0eea2ef7bbbaeb4
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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