Potassium Hydroxide → HCID 54041432, compound

HRID 4994Notes

Reaction equation

HRID 4994 reaction equation
[CH3:1][CH:2]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]2[C:4](=[C:5]([OH:18])[CH:6]=[CH:7][C:8]=2[CH3:17])[C:3]1=[O:19].[CH2:20](Br)[CH:21]=[CH:22][CH3:23].[OH-].[K+]>CC(C)=O>[CH3:1][CH:2]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]2[C:4](=[C:5]([O:18][CH2:20][CH:21]=[CH:22][CH3:23])[CH:6]=[CH:7][C:8]=2[CH3:17])[C:3]1=[O:19]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 1224142-Butene, 1-bromo-HCID 148347312,3-dihydro-2,4-dimethyl-3-phenyl-7-hydroxy-1H-inden-1-one

Product 1

HCID 54041432HCID 54041432, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 19.0 g of 2,3-dihydro-2,4-dimethyl-3-phenyl-7-hydroxy-1H-inden-1-one, 13.98 of crotyl bromide and 5.47 g of potassium hydroxide in 200 ml of acetone was heated and refluxed under stirring condition. After the reaction was completed, the reaction mixture was concentrated and extracted with ethyl acetate, then the extract was washed with water and with an aqueous solution saturated with sodium chloride, then dried. The extract was concentrated by removing the solvent under a reduced pressure, then recrystallized from methanol to obtain 11.8 g of 2,3-dihydro-2,4-dimethyl-3-phenyl-7-crotyloxy-1H-inden-1-one as in the form of cis-trans mixture. Colorless stick-like crystals. Melting point: 138.5°-139.5° C.

Workup

  1. temperaturerefluxed
  2. concentrationthe reaction mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washthe extract was washed with water and with an aqueous solution saturated with sodium chloride
  5. customdried
  6. concentrationThe extract was concentrated
  7. customby removing the solvent under a reduced pressure
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-052823d5aace48c1ba767bdcf24f3608
Source dataset
uspto-grants-1993_09
Patent number
US05242919

Reaction notes

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