Water → E-1-crotonoyl-2,2,6-trimethylcyclohexane

HRID 1076296Notes

Reaction equation

HRID 1076296 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:7][CH2:6][CH2:5][C@H:4]([CH3:8])[C@@H:3]1[CH2:9][CH2:10][CH:11](O)[CH3:12].[OH2:15]>C1C=CC=CC=1>[C:9]([CH:3]1[CH:4]([CH3:8])[CH2:5][CH2:6][CH2:7][C:2]1([CH3:14])[CH3:1])(=[O:15])/[CH:10]=[CH:11]/[CH3:12]

Participants

4

Reactant 2

HCID 962Water2×HCID 59957946cis-1-(2,2,6-Trimethylcyclohexyl)-3-butanol

Product 1

HCID 21989633E-1-crotonoyl-2,2,6-trimethylcyclohexane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 320 g (1.5 moles) of the ketol prepared in Example 2 in 1000 ml of benzene containing 2 g p-toluenesulphonic acid is heated in an apparatus for azeotropical water separation (Dean-Stark) till no more water separates. The reaction mixture is washed with a solution of sodium bicarbonate till neutral reaction and dried over anhydrous sodium sulfate. The solvent is removed by distillation at reduced pressure and the residue is distilled through a short Vigreux column. The product, cis, E-1-crotonoyl-2,2,6-trimethyl-cyclohexane (III, contains about 10% of the trans isomer) is collected at 76°C/1 mm; yield 273 g (94%). Recrystallization from pentane gives cis, E-1-crotonoyl-2,2,6-trimethylcyclohexane in high purity (m.p. 27°-28°C).

Workup

  1. washThe reaction mixture is washed with a solution of sodium bicarbonate till neutral reaction
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent is removed by distillation at reduced pressure
  4. distillationthe residue is distilled through a short Vigreux column
  5. customis collected at 76°C/1 mm
  6. customRecrystallization from pentane

Sources & evidence

ORD record
ord-c82ba37fdbc9447a8d54c12d24d9acd0
Source dataset
uspto-grants-1976_05
Patent number
US03956392

Reaction notes

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