6-Methyl-5-hepten-2-one → 3,7-Nonadienoic acid, 4,8-dimethyl-, methyl ester

HRID 2164186Notes

Reaction equation

HRID 2164186 reaction equation
[CH3:1]C(C)=CCCC(=O)C.[CH3:10][C:11]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:12][CH2:13][C:14]([OH:16])=[O:15].[Cl-].[C:24]([CH2:27]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(O)=O>CS(C)=O>[CH3:10][C:11]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:12][CH2:13][C:14]([O:16][CH3:1])=[O:15].[CH3:10][C:11]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:12][CH2:13][C:14]([O:16][CH2:24][CH3:27])=[O:15]

Participants

6

Reactant 3

HCID 98626-Methyl-5-hepten-2-oneHCID 10270534(2-Carboxyethyl)triphenylphosphonium chlorideHCID 54343890HCID 54343890, compound

Product 2

HCID 5497503,7-Nonadienoic acid, 4,8-dimethyl-, methyl esterHCID 53706627Ethyl 4,8-dimethylnona-3,7-dienoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6-Methyl-5-hepten-2-one is converted into 4,8-dimethylnona-3,7-dienoic acid by reaction with β-carboxyethyltriphenylphosphonium chloride in dimethylsulfoxide using the method of H. S. Corey et al., J. Am. Chem. Soc. 86, 1884 (1964). The trans and cis isomer can be separated by chromatography at this point or a mixture of the two isomers employed in further reactions. The acid is then converted into the acid chloride using thionyl chloride at roomm temperature or slightly higher. The acid chloride is then treated with an alcohol, such as methanol or ethanol, at a temperature of about 40° for a few minutes to yield the ester, methyl 4,8-dimethylnona-3,7-dienoate and ethyl 4,8-dimethylnona-3,7-dienoate.

Workup

  1. customThe trans and cis isomer can be separated by chromatography at this point
  2. additiona mixture of the two isomers
  3. additionThe acid chloride is then treated with an alcohol, such as methanol or ethanol, at a temperature of about 40° for a few minutes

Sources & evidence

ORD record
ord-f0581ef25f564578bbff1248f7c1f3af
Source dataset
uspto-grants-1979_01
Patent number
US04137273

Reaction notes

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