Methyl Acrylate → HCID 54032900, compound

HRID 1076312Notes

Reaction equation

HRID 1076312 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][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.[C:29]([O:33]C)(=[O:32])[CH:30]=[CH2:31]>CO.C(COC)OC>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH:14]=[CH:13][CH2:12][C:11]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:10](=[O:28])[CH:9]=[CH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:31][CH2:30][C:29]([OH:33])=[O:32])=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 7294Methyl AcrylateHCID 53765659HCID 53765659, compound

Product 1

HCID 54032900HCID 54032900, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Triton B (1 ml., 40% in MeOH) is added to a stirred solution of 1,7-bis-(p-chlorophenyl)-4-phenyl-1,6-heptadien-3-one (16.10 g., 0.039 mole) in glyme (150 ml.), followed by addition of methyl acrylate (3.87 g., 0.045 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 (20 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 (25 ml.) and the solid (yellowish) that precipitates is filtered and air-dried; yield 16.5 g., m.p. 75°-173°C. Several recrystallizations from n-butyl chloride gives material with m.p. 178.5°-180°C.

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 (20 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. customthe solid (yellowish) that precipitates
  15. filtrationis filtered
  16. customair-dried
  17. customSeveral recrystallizations from n-butyl chloride
  18. customgives material with m.p. 178.5°-180°C.

Sources & evidence

ORD record
ord-ab56a9988c4443b9b58499168126b0fa
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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