Methyl Acrylate → HCID 53839935, compound

HRID 1076324Notes

Reaction equation

HRID 1076324 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]([CH3:21])=[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>[CH3:21][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 54524986HCID 54524986, compound

Product 1

HCID 53839935HCID 53839935, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Triton B (1 ml., 40% in MeOH) is added to a stirred suspension of 1-(p-chlorophenyl)-4-phenyl-7-(p-methylphenyl)-1,6-heptadien-3-one (14.55 g., 0.038 mole) in glyme (150 ml.) followed by addition of methyl acrylate (3.87 g., 0.045 mole) in glyme (25 ml.). The mixture is warmed slightly to obtain solution then is stirred for 24 to 48 hours. The solvent is removed under reduced pressure and water (1000 ml.) and dilute hydrochloric acid is added to the residue. The organic material is extracted into ether and these extracts are washed with water, saturated brine and dried (MgSO4). After removal of the solvent the residue is heated with a solution of 20% sodium hydroxide (20 ml.) in methanol (800 ml.) on the steam bath for 24 hours. The methanol is removed in vacuo and the residue is dissolved in a large volume of water. Extraction with ether removes unreacted ketone. Ether is expelled from the aqueous phase by warming and dilute hydrochloric acid is added. The solid that separates is collected, washed well with water, and air-dried, yield 10.43 g., m.p. 170°-180°C. Recrystallization from acetonitrile gives material with m.p. 182°-185°C.

Workup

  1. temperatureThe mixture is warmed slightly
  2. customto obtain solution
  3. customThe solvent is removed under reduced pressure and water (1000 ml.) and dilute hydrochloric acid
  4. additionis added to the residue
  5. extractionThe organic material is extracted into ether
  6. washthese extracts are washed with water, saturated brine
  7. dry with materialdried (MgSO4)
  8. customAfter removal of the solvent the residue
  9. temperatureis heated with a solution of 20% sodium hydroxide (20 ml.) in methanol (800 ml.) on the steam bath for 24 hours
  10. customThe methanol is removed in vacuo
  11. dissolutionthe residue is dissolved in a large volume of water
  12. extractionExtraction with ether
  13. customremoves unreacted ketone
  14. temperatureby warming
  15. additiondilute hydrochloric acid is added
  16. customThe solid that separates is collected
  17. washwashed well with water
  18. customair-dried
  19. customRecrystallization from acetonitrile
  20. customgives material with m.p. 182°-185°C.

Sources & evidence

ORD record
ord-36a16c82faf74fb9a35ceb7df35c1e06
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

Loading…