Benzene → HCID 548881, compound

HRID 1981963Notes

Reaction equation

HRID 1981963 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[CH:10]1[CH:15]=[CH:14]C=CC=1.[CH3:16]O>>[CH:16](=[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C:1]1=[O:7])[CH:15]([CH3:14])[CH3:10]

Participants

5

Reactant 4

HCID 241BenzeneHCID 887MethanolHCID 7967CyclohexanoneHCID 14798Sodium Hydroxide

Product 1

HCID 548881HCID 548881, compoundYield 37%

Procedure

While stirring a mixture of 52.5 g (0.536 mol) of cyclohexanone and 13.5 g (0.188 mol) of isobutylaldehyde, a solution prepared by dissolving 2.2 g of sodium hydroxide in 50 ml of methanol is dropwise added to the mixture at a temperature of from room temperature to 40° C., and reacted at room temperature for 2 hours. After the reaction, 20 ml of benzene was added, and the reaction mixture was washed three times with 100 ml of water. From the organic layer, benzene and unreacted cyclohexanone were recovered by distillation, and the distillation was continued, whereby 2-isobutylidene cyclohexanone was obtained in the yield of 37% (based on the isobutylaldehyde) under reduced pressure of 6 mmHg at a temperature of from 95° to 105° C.

Workup

  1. customa solution prepared
  2. additionis dropwise added to the mixture at a temperature of from room temperature to 40° C.
  3. customreacted at room temperature for 2 hours
  4. additionwas added
  5. washthe reaction mixture was washed three times with 100 ml of water
  6. distillationFrom the organic layer, benzene and unreacted cyclohexanone were recovered by distillation
  7. distillationthe distillation

Sources & evidence

ORD record
ord-9661abfc267e472fb6b06a968c732395
Source dataset
uspto-grants-1986_06
Patent number
US04594438

Reaction notes

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