4-(Acetyloxy)-2-butanone → 2,3,6-Trimethylcyclohex-2-en-1-one

HRID 65808

Reaction equation

HRID 65808 reaction equation
C(O[CH2:5][CH2:6][C:7](=O)[CH3:8])(=O)C.[CH3:10][O-:11].[Na+]>CO>[CH3:5][C:6]1[C:10](=[O:11])[CH:7]([CH3:8])[CH2:6][CH2:5][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 1391004-(Acetyloxy)-2-butanoneHCID 10942334Sodium Methoxide

Product 1

HCID 30168432,3,6-Trimethylcyclohex-2-en-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

130 g of 1-acetoxybutan-3-one and sodium methylate solution in methanol are dripped in the course of one hour from separate supply vessels while stirring into 400 g of boiling diethyl ketone at such a rate that the reaction mixture remains constantly alkaline. A total of 190 g of a 30% by weight sodium methylate solution is used up in this way. The whole is then heated under reflux for another hour and then neutralized with glacial acetic acid. Deposited sodium acetate is filtered off and the filtrate is subjected to fractional distillation. 81 g of 2,3,6-trimethyl-2-cyclohexen-1-one is obtained as well as traces of 4-methyl-3-ethyl-2-cyclohexen-1-one. The yield with reference to 1-acetoxybutan-3-one is 59%.

Workup

  1. customare dripped in the course of one hour
  2. customfrom separate supply vessels
  3. temperatureThe whole is then heated
  4. temperatureunder reflux for another hour
  5. filtrationDeposited sodium acetate is filtered off
  6. distillationthe filtrate is subjected to fractional distillation

Sources & evidence

ORD record
ord-6378b9e4c99d40c6811d8c8750d9496a
Source dataset
uspto-grants-1978_12
Patent number
US04128728

Linked notes

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