Potassium Hydroxide → 3-(2-Ethylhexanoyloxy)-5,5-dimethyl-2-(2',5'-dimethylphenyl)-2-cyclohexenone

HRID 65285

Reaction equation

HRID 65285 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH:9]1[C:14](=[O:15])[CH2:13][C:12]([CH3:17])([CH3:16])[CH2:11][C:10]1=[O:18].[OH-].[K+].[CH2:21]([CH:23]([CH2:27][CH2:28][CH2:29][CH3:30])[C:24](Cl)=[O:25])[CH3:22]>C1C=CC=CC=1.C1CC2OCCOCCOC3C(OCCOCCOC2CC1)CCCC3.CCOCC>[CH2:21]([CH:23]([CH2:27][CH2:28][CH2:29][CH3:30])[C:24]([O:18][C:10]1[CH2:11][C:12]([CH3:16])([CH3:17])[CH2:13][C:14](=[O:15])[C:9]=1[C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[CH3:1])=[O:25])[CH3:22]

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 791032-Ethylhexanoyl chlorideHCID 128766022-(2',5'-Dimethylphenyl)-5,5-dimethyl-1,3-cyclohexanedione

Product 1

HCID 202065103-(2-Ethylhexanoyloxy)-5,5-dimethyl-2-(2',5'-dimethylphenyl)-2-cyclohexenoneYield 92%

Reagents, catalysts & solvents 3

HCID 85955Dicyclohexano-18-crown-6CatalystHCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A suspension of 1.50 g (6.14 mmol) of 2-(2',5'-dimethylphenyl)-5,5-dimethyl-1,3-cyclohexanedione in 15 ml of dry benzene was prepared and 0.49 g (7.37 mmol) of 85% powered potassium hydroxide was added, followed by 1 drop of dicyclohexyl-18-crown-6-ether. After stirring for 30 minutes, 1.20 (7.37 mmol) of 2-ethylhexanoyl chloride was added, and the reaction mixture refluxed for 12 hrs. The reaction mixture was cooled to room temperature, taken up in 150 ml ether and 50 ml of water, washed three times with 0.25N NaOH, two times with water, two times with 6N HCl, and one more with water. The ether solution was dried and stripped to leave 2.10 g (92% yield) of 3-(2-ethylhexanoyloxy)-5,5-dimethyl-2-(2',5'-dimethylphenyl)-2-cyclohexenone as a clear, colorless oil.

Workup

  1. customwas prepared
  2. temperaturethe reaction mixture refluxed for 12 hrs
  3. wash50 ml of water, washed three times with 0.25N NaOH, two times with water, two times with 6N HCl, and one more with water
  4. dry with materialThe ether solution was dried

Sources & evidence

ORD record
ord-34b48e88f482444b8bff393b770af19f
Source dataset
uspto-grants-1986_09
Patent number
US04613617

Linked notes

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