Sulfuric Acid → 4,4-Diethylcyclohex-2-en-1-one

HRID 1924813Notes

Reaction equation

HRID 1924813 reaction equation
[CH2:1]([CH:3]([CH2:6][CH3:7])[CH:4]=O)[CH3:2].[CH3:8][C:9]([CH:11]=[CH2:12])=[O:10].OS(O)(=O)=O>C(Cl)(Cl)Cl>[CH2:1]([C:3]1([CH2:6][CH3:7])[CH2:4][CH2:8][C:9](=[O:10])[CH:11]=[CH:12]1)[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 6570Methyl vinyl ketone2×HCID 73592-Ethylbutyraldehyde

Product 1

HCID 124849234,4-Diethylcyclohex-2-en-1-oneYield 104.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-ethylbutyraldehyde (12.3 mL, 100 mmol), methylvinylketone (5.6 mL, 67.3 mmol) and H2SO4 (0.07 mL) is stirred at 40° C. overnight. Another portion of methylvinylketone (5.6 mL, 67.3 mmol) and H2SO4 is added and stirring is continued at 40° C. for 2 d. The yellow solution is diluted with chloroform and the solvent is removed again under reduced pressure. The crude product is purified by vacuum distillation to give 4,4-diethyl-cyclohex-2-enone (10.7 g) as a colourless oil; Bp11 mbar=88° C.; 1H NMR (CDCl3): δ 6.71 (d, J=10.0 Hz, 1H), 5.92 (d, J=10.5 Hz, 1H), 2.42 (t, J=7.0 Hz, 2H), 1.84 (t, J=7.0 Hz, 2H), 1.57-1.40 (m, 4H), 0.87 (t, J=7.6 Hz, 6H).

Workup

  1. stirringstirring
  2. waitis continued at 40° C. for 2 d
  3. customthe solvent is removed again under reduced pressure
  4. distillationThe crude product is purified by vacuum distillation

Sources & evidence

ORD record
ord-4f47f6a4ca574256a9ed469582f503b8
Source dataset
uspto-grants-2012_05
Patent number
US08178562B2

Reaction notes

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