Isopropanol → (E)-4-(2-chloro-4-biphenylyl)-3-pentene-2-ol

HRID 1605657Notes

Reaction equation

HRID 1605657 reaction equation
[Cl:1][C:2]1[C:7](/C(/C)=C/C(=O)C)=[CH:6][CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:20][CH:21]([O-:23])[CH3:22].[CH3:24][CH:25]([O-])C.CC([O-])C.[Al+3].C(O)(C)C>>[Cl:1][C:2]1[CH:7]=[C:6](/[C:24](/[CH3:25])=[CH:20]/[CH:21]([OH:23])[CH3:22])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 11143Aluminum isopropoxideHCID 68133289(E)-4-(2-chloro-biphenylyl)-3-pentene-2-one

Product 1

HCID 21547087(E)-4-(2-chloro-4-biphenylyl)-3-pentene-2-ol

Procedure

80.0 Gm (0.296 mol) of (E)-4-(2-chloro-biphenylyl)-3-pentene-2-one were gently refluxed with 68.0 gm (0.333 mol) of aluminum isopropylate and 300 ml (3.92 mols) of isopropanol in a dry distillation apparatus with a 60-cm-Vigreux-column, such that only about 5 drops were distilled off per minute. After about 5 hours no acetone was found to be present in the distillate (using hydrochloric acid 2,4-dinitrophenyl-hydrazine solution) and in the reaction mixture no unreacted starting material could be found (by thin-layer-chromatography). The isopropanol was distilled off in a weak vacuum. The residue was hydrolyzed by addition of 300 gm of crushed ice. The ethereal (upper) phase, was decanted, and the aluminum hydrozide slurry was carefully washed with ether several times. The combined extracts were washed with water, with aqueous 5% sodium hydroxide and again with water, and dried over sodium sulfate. The solvent was evaporated in vacuo and the residue was recrystallized once from petroleum ether/ethyl acetate (ratio by volume = 4:1). Yield: 64.0 gm (79% of theory) of colorless crystals, m.p. 86°C.

Workup

  1. distillationwere distilled off per minute
  2. distillationThe isopropanol was distilled off in a weak vacuum
  3. additionThe residue was hydrolyzed by addition of 300 gm of crushed ice
  4. customThe ethereal (upper) phase, was decanted
  5. washthe aluminum hydrozide slurry was carefully washed with ether several times
  6. washThe combined extracts were washed with water, with aqueous 5% sodium hydroxide and again with water
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was evaporated in vacuo
  9. customthe residue was recrystallized once from petroleum ether/ethyl acetate (ratio by volume = 4:1)

Sources & evidence

ORD record
ord-df8a3c75c02c4349beb8bed63ebf6f85
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

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