Methyl Acrylate → HCID 54185517, compound

HRID 1076330Notes

Reaction equation

HRID 1076330 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=[O:25])[CH:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[C:26]([O:30]C)(=[O:29])[CH:27]=[CH2:28]>CO.C(COC)OC>[CH2:12]([C:11]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:10](=[O:25])[CH:9]=[CH:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH2:28][CH2:27][C:26]([OH:30])=[O:29])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 7294Methyl AcrylateHCID 544687331-(4-Chlorophenyl)-4,5-diphenyl-1-penten-3-one

Product 1

HCID 54185517HCID 54185517, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Triton B (2 ml., 40% in MeOH) is added to a stirred solution of 1-(p-chlorophenyl)-4,5-diphenyl-1-penten-3-one (17.33 g., 0.05 mole) in glyme (200 ml.) followed by addition of methyl acrylate (4.73 g., 0.055 mole) in glyme (50 ml.). The solution is stirred for 96 hours and the solvent is removed under reduces pressure. The residue is dissolved in methanol (500 ml.) and a 20% sodium hydroxide solution (25 ml.) is added. After an additional 24 hours, the methanol is evaporated in vacuo and the residue is dissolved in water. Extraction with ether removes unreacted ketone. Acidification produces 16.18 g., m.p. 160°-170°C. when collected and air-dried. Recrystallization from butyl chloride gives material with m.p. 173°-176°C.

Workup

  1. customthe solvent is removed
  2. dissolutionThe residue is dissolved in methanol (500 ml.)
  3. additiona 20% sodium hydroxide solution (25 ml.) is added
  4. waitAfter an additional 24 hours
  5. customthe methanol is evaporated in vacuo
  6. dissolutionthe residue is dissolved in water
  7. extractionExtraction with ether
  8. customremoves unreacted ketone
  9. customAcidification produces 16.18 g
  10. custom, m.p. 160°-170°C. when collected
  11. customair-dried
  12. customRecrystallization from butyl chloride
  13. customgives material with m.p. 173°-176°C.

Sources & evidence

ORD record
ord-5c15301741634e3782dcde54c48bef35
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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