Water → 4-Butyl-4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

HRID 262441Notes

Reaction equation

HRID 262441 reaction equation
CC1C[O:5][C:4]2([CH2:11][C:10]([CH3:13])([CH3:12])[C:9](=[O:14])[C:8]([CH3:15])=[CH:7]2)O1.[CH2:16]([Li])[CH2:17][CH2:18][CH3:19].O.[Li]>CCCCCC>[CH2:16]([C:9]1([OH:14])[C:10]([CH3:12])([CH3:13])[CH2:11][C:4](=[O:5])[CH:7]=[C:8]1[CH3:15])[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 3028194LithiumHCID 132091832,7,9,9-Tetramethyl-1,4-dioxaspiro[4,5]dec-6-en-8-oneHCID 178418339Butyllithium

Product 1

HCID 147596004-Butyl-4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

A solution of 20 g of 2,7,9,9-tetramethyl-1,4-dioxaspiro[4,5]dec-6-en-8-one (prepared by the method of Example III) in hexane is stirred while a solution of n-butyl lithium in hexane is added dropwise. When no additional exotherm occurs, the addition is stopped and the mixture is stirred for about 15 minutes. Water is added with stirring to hydrolyze the lithium salt. The organic layer is separated, and the hexane is allowed to evaporate leaving oily crystals which are recrystallized from cyclohexane yielding 10 g of 4-butyl-4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one, melting point 90°-93° C. The compound exhibits the following spectral characteristics:

Workup

  1. additionis added dropwise
  2. additionthe addition
  3. stirringwith stirring
  4. customThe organic layer is separated
  5. customto evaporate
  6. customleaving oily crystals which
  7. customare recrystallized from cyclohexane yielding 10 g of 4-butyl-4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one, melting point 90°-93° C

Sources & evidence

ORD record
ord-5e76aea4434148f9acb064f4d15b5983
Source dataset
uspto-grants-1979_05
Patent number
US04154763

Reaction notes

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