Potassium Hydroxide → 1-(2,2-Dimethyl-6-methylenecyclohexyl)-2-buten-1-one

HRID 1579753Notes

Reaction equation

HRID 1579753 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH:7]2[C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10][CH2:9][C:8]2=[CH2:15])[O:4]N=1.[OH-].[K+]>C(O)C.[Ni]>[CH2:15]=[C:8]1[CH2:9][CH2:10][CH2:11][C:12]([CH3:14])([CH3:13])[CH:7]1[C:5](=[O:4])[CH:6]=[CH:2][CH3:1]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 21524336HCID 21524336, compound

Product 1

HCID 566317481-(2,2-Dimethyl-6-methylenecyclohexyl)-2-buten-1-oneYield 104.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

4.1 g of 3-methyl-5-[2-methylene-6,6-dimethyl-cyclohexyl]-isoxazole in 10 ml of anhydrous ethanol were subjected to a hydrogenation in the presence of a small amount of Raney nickel and of KOH. After absorption of 440 ml of hydrogen (corresponding to about 90% of the theoretical amount) the solution was filtered, washed until neutrality and concentrated to yield an oily residue (4 g). By separation by means of vapour phase chromatography ("Carbowax" column, 1.5 m) there was obtained in a yield of 80% 2-methylene-6,6-dimethyl-1-[3-amino-but-2-enoyl]-cyclohexane. nD = 1.5448; d20 = 1.009.

Workup

  1. customAfter absorption of 440 ml of hydrogen (corresponding to about 90% of the theoretical amount) the solution
  2. filtrationwas filtered
  3. washwashed until neutrality
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3e272f2516504694b90c77bd63e56427
Source dataset
uspto-grants-1976_01
Patent number
US03931323

Reaction notes

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