Methyl Isobutyl Ketone → 2,8,12-Trimethyl-5,7,11-tridecatrien-4-one

HRID 224760

Reaction equation

HRID 224760 reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][C:7](=[CH:9][CH:10]=O)[CH3:8])[CH3:3].[CH2:12]([C:16]([CH3:18])=[O:17])[CH:13]([CH3:15])[CH3:14]>O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[CH3:14][CH:13]([CH2:12][C:16](=[O:17])[CH:18]=[CH:10][CH:9]=[C:7]([CH3:8])[CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])[CH3:15]

Participants

4

Reactant 2

HCID 7909Methyl Isobutyl KetoneHCID 88433,7-Dimethylocta-2,6-Dienal

Product 1

HCID 543290252,8,12-Trimethyl-5,7,11-tridecatrien-4-oneYield 32.5%

Reagents, catalysts & solvents 1

HCID 2724192Zinc acetate (USP)Catalyst

Conditions

Temperature
160 °C

Procedure

Into a 2 liter autoclave are charged citral (152 grams), methyl isobutyl ketone (500 grams) and zinc acetate dihydrate (38 grams). The reaction mixture is heated at 160° C. for a period of 12 hours. After filtering the catalyst the organic layer is washed with 10% salt solution. Distillation yielding 76 grams (32% yield) of the product, B.P. 126°-141° C./1 mmHg.

Workup

  1. filtrationAfter filtering the catalyst the organic layer
  2. washis washed with 10% salt solution
  3. distillationDistillation

Sources & evidence

ORD record
ord-7dab42019d5845d293961498223c3dbd
Source dataset
uspto-grants-1980_11
Patent number
US04234518

Linked notes

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