Acetic Acid → HCID 54441028, compound

HRID 1076321Notes

Reaction equation

HRID 1076321 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=[O:27])[CH:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:12][CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.[C:28]([O:32]CC)(=[O:31])[CH:29]=[CH2:30].C(O)(=O)C.[OH-].[Na+]>CO.C(COC)OC.O>[CH2:12]([C:11]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([C:10](=[O:27])[CH:9]=[CH:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH2:30][CH2:29][C:28]([OH:32])=[O:31])[CH:13]=[CH:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 8821Ethyl AcrylateHCID 14798Sodium HydroxideHCID 53690556HCID 53690556, compound

Product 1

HCID 54441028HCID 54441028, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Triton B (0.2 ml., 40% in MeOH) is added to a stirred solution of 1-(p-chlorophenyl)4,7-diphenyl-1,6-heptadien-3-one (3.72 g., 0.01 mole) in glyme (25 ml.), followed by addition of ethyl acrylate (1.11 g., >0.01 mole). After stirring for 24 hours, glacial acetic acid (0.5 ml.) is added and the solvent removed under reduced pressure. The residue is mixed with a solution of sodium hydroxide (0.80 g., 0.02 mole) in water (15 ml.) and methanol (150 ml.) and stirred for 24 hours. The methanol is removed in vacuo and the residue is dissolved in water (200 ml.). Extraction with ether removes unreacted ketone. Ether is expelled from the aqueous phase and it is acidified to Congo Red with dilute hydrochloric acid. The off-white solid that separates is collected, washed well with water, and air-dried, yield 3 g. Recrystallization from benzene-hexane gives material with m.p. 135°-140°C.

Workup

  1. customthe solvent removed under reduced pressure
  2. stirringstirred for 24 hours
  3. customThe methanol is removed in vacuo
  4. dissolutionthe residue is dissolved in water (200 ml.)
  5. extractionExtraction with ether
  6. customremoves unreacted ketone
  7. customThe off-white solid that separates is collected
  8. washwashed well with water
  9. customair-dried
  10. customRecrystallization from benzene-hexane
  11. customgives material with m.p. 135°-140°C.

Sources & evidence

ORD record
ord-dbb5deda208d4a8588a40115f2c58037
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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