Cyclohexane → 4,8-Dimethylnona-3,7-dien-2-one

HRID 1580180Notes

Reaction equation

HRID 1580180 reaction equation
[CH3:1][C:2](=[CH2:14])[CH2:3][C:4]([O:10]CCC)(OCCC)[CH3:5].[CH3:15][C:16]([CH3:20])=[CH:17][CH2:18]O.C1CCCCC1>C(O)=O>[CH3:5][C:4]([CH2:10][CH2:18][CH:17]=[C:16]([CH3:20])[CH3:15])=[CH:3][C:2](=[O:14])[CH3:1]

Participants

5

Reactant 3

HCID 8078CyclohexaneHCID 111733-Methyl-2-buten-1-OLHCID 21565207HCID 21565207, compound

Product 1

HCID 5496634,8-Dimethylnona-3,7-dien-2-oneYield 89%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

In an autoclave, a mixture of 120 parts of 4-methyl-2,2-di-n-propoxy-4-pentene, 50 parts of prenol and 170 parts of cyclohexane is heated with 3.4 parts of formic acid for 4 hours at 160°C. Fractional distillation gives 57.5 parts of 4,8-dimethyl-3,7-nonadien-2-one, equivalent to a yield of 89% and a conversion of 67% based on prenol.

Workup

  1. distillationFractional distillation

Sources & evidence

ORD record
ord-9d38c3a0a954463e8a8f0537ebfe448c
Source dataset
uspto-grants-1976_01
Patent number
US03932462

Reaction notes

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