4-Hydroxybiphenyl → HCID 13254741, compound

HRID 2291719Notes

Reaction equation

HRID 2291719 reaction equation
Cl[CH2:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH:5]=[CH2:6].C(=O)([O-])[O-].[K+].[K+].[OH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][CH:18]=1>CC(C)=O>[C:20]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:18][C:17]([O:16][CH2:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH:5]=[CH2:6])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 71034-HydroxybiphenylHCID 11430Potassium CarbonateHCID 13102421HCID 13102421, compound

Product 1

HCID 13254741HCID 13254741, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

196.5 g (1.34 mol) of 5-chloro-3,3-dimethylpent-1-en-4-one were added dropwise to a mixture of 184.9 g (1.34 mol) of potassium carbonate and 227.8 (1.34 mol) of 4-hydroxybiphenyl in 1,000 ml of boiling acetone, in the course of one hour. The mixture was heated to the boil after 5 hours, allowed to cool to room temperature, and filtered off from the precipitated potassium chloride. The oil which remained after the filtrate had been concentrated was taken up in 1,000 ml of ethyl acetate. The solution was washed twice with 150 ml each of 10% strength sodium carbonate solution and water, and dried over anhydrous sodium sulphate, and the solvent was distilled off. Residual amounts of solvent were stripped off at 0.13 mbar (bath temperature: 180° C.). 357.2 (95% of theory) of 5-(biphenyl-4-yloxy)-3,3-dimethylpent-1-en-4-one of melting point 42° to 44° C. were obtained in this manner.

Workup

  1. temperatureThe mixture was heated to the boil after 5 hours
  2. filtrationfiltered off from the precipitated potassium chloride
  3. concentrationhad been concentrated
  4. washThe solution was washed twice with 150 ml each of 10% strength sodium carbonate solution and water
  5. dry with materialdried over anhydrous sodium sulphate
  6. distillationthe solvent was distilled off
  7. customwere stripped off at 0.13 mbar (bath temperature: 180° C.)

Sources & evidence

ORD record
ord-186e71f50cbf42de90eb4f811c2ef17d
Source dataset
uspto-grants-1989_01
Patent number
US04797499

Reaction notes

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