Isopropanol → HCID 21547078, compound

HRID 1605651Notes

Reaction equation

HRID 1605651 reaction equation
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9](=[O:11])[CH3:10])=[CH:3][CH:2]=1.[Al].CC(C)[O-].C(O)(C)C>>[C:1]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][C:4](/[CH:7]=[CH:8]/[CH:9]([OH:11])[CH3:10])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 5792363(E)-4-(1,1'-Biphenyl)-4-yl-2-buten-2-oneHCID 86733237HCID 86733237, compound

Product 1

HCID 21547078HCID 21547078, compound

Procedure

13.0 Gm (0.0585 mol) of (E)-4-(4-biphenylyl)-3-butene-2-one were gently refluxed with 12.5 gm (0.0612 mol) of aluminum-isopropoxide and 190 ml (2.48 mol) of isopropanol in a dry distillation apparatus with a 60-cm-Vigreux-column, in such a way that only about 5 drops were distilled off per minute. After about 5 hours no acetone was found to be present in the distillate (by use of hydrochloric 2,4-dinitrophenyl-hydrazine-solution). In the reaction mixture, columnchromatography showed no starting material was present. The isopropanol was distilled off in a weak vacuum, the residue was hydrolyzed by addition of 50 gm of crushed ice and 34 ml of 6 N hydrochloric acid. The reaction mixture was exhaustively extracted with ethyl acetate, the combined extracts were washed with water, with 5% sodium hydroxide solution and again with water, and dried over sodium sulfate. The solvent was evaporated in vacuo and the residue was recrystallized, once from cyclohexane/ethyl acetate (ratio by volume: 9:1) and once from benzene. Yield: 11.0 gm (84% of theory) of colorless crystals, m.p. 138°-139°C.

Workup

  1. distillationin such a way that only about 5 drops were distilled off per minute
  2. distillationThe isopropanol was distilled off in a weak vacuum
  3. additionthe residue was hydrolyzed by addition of 50 gm of crushed ice and 34 ml of 6 N hydrochloric acid
  4. extractionThe reaction mixture was exhaustively extracted with ethyl acetate
  5. washthe combined extracts were washed with water, with 5% sodium hydroxide solution and again with water
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated in vacuo
  8. customthe residue was recrystallized, once from cyclohexane/ethyl acetate (ratio by volume: 9:1) and once from benzene

Sources & evidence

ORD record
ord-6d0a1ef677e6477a8e3d4f49c4b7465c
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

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