tert-Butanol → cis t-Butyl 3,7,11-trimethyldodeca-2,4-dienoate

HRID 2397287Notes

Reaction equation

HRID 2397287 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6](/[CH:11]=[CH:12]\[CH2:13][CH:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:7][C:8]([OH:10])=[O:9].[C:22](O)([CH3:25])([CH3:24])[CH3:23]>>[CH3:5][C:6](/[CH:11]=[CH:12]\[CH2:13][CH:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:7][C:8]([O:10][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:9]

Participants

4

Reactant 3

HCID 6386tert-ButanolHCID 24386Thionyl ChlorideHCID 86734009cis 3,7,11-Trimethyldodeca-2,4-dienoic acid

Product 1

HCID 86734713cis t-Butyl 3,7,11-trimethyldodeca-2,4-dienoate

Procedure

One gram of thionyl chloride is added with stirring at room temperature to 0.5 g. of trans/cis 3,7,11-trimethyldodeca-2,4-dienoic acid and the mixture heated at about 50° for 10 minutes. Excess thionyl chloride is removed by evaporation and then t-butyl alcohol (about 2 equivalents) is added and the mixture heated at about 50° for about 5 minutes. Excess t-butyl alcohol is removed by evaporation to yield trans/cis t-butyl 3,7,11-trimethyldodeca-2,4-dienoate which is purified by chromatography.

Workup

  1. customExcess thionyl chloride is removed by evaporation
  2. temperaturethe mixture heated at about 50° for about 5 minutes
  3. customExcess t-butyl alcohol is removed by evaporation

Sources & evidence

ORD record
ord-c0f7f61748cc4fcab4a2260868091f70
Source dataset
uspto-grants-1977_05
Patent number
US04021461

Reaction notes

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