Sodium → Cyclobutanone, 3-(4-chlorophenyl)-2,2-dimethyl-

HRID 2119060Notes

Reaction equation

HRID 2119060 reaction equation
[Na].Br[CH:3]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[C:4]([CH3:9])([CH3:8])[C:5](=[O:7])[CH3:6]>C(O)C.O>[CH3:8][C:4]1([CH3:9])[CH:3]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:6][C:5]1=[O:7]

Participants

5

Reactant 2

HCID 5360545SodiumHCID 132771714-Bromo-4-(4-chlorophenyl)-3,3-dimethylbutan-2-one

Product 1

HCID 11789026Cyclobutanone, 3-(4-chlorophenyl)-2,2-dimethyl-Yield 65%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

0.91 g (0.04 mol) of sodium is dissolved in 100 ml of ethanol and, at 20° C., 10.5 g (0.036 mol) of 1-bromo-1-(4-chlorophenyl)-2,2-dimethyl-3-butanone in 20 ml of ethanol are added. The reaction mixture is stirred at 20° C. for about 15 hours, diluted with water and neutralized. It is extracted with methylene chloride, dried with sodium sulphate and the solvent is distilled off from the filtrate under waterpump vacuum. The residue is purified by distillation under high vacuum. 4.8 g (65% of theory) of 2,2-dimethyl-3-(4-chlorophenyl)cyclobutanone of boiling point 98° to 107° C./0.05 mbar are obtained.

Workup

  1. extractionIt is extracted with methylene chloride
  2. dry with materialdried with sodium sulphate
  3. distillationthe solvent is distilled off from the filtrate under waterpump vacuum
  4. distillationThe residue is purified by distillation under high vacuum

Sources & evidence

ORD record
ord-4f096bbb34514163b326c952b86169d4
Source dataset
uspto-grants-1987_07
Patent number
US04681952

Reaction notes

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