Benzene → Isobutyl 3,7,11-trimethyldodeca-2,4-dienoate

HRID 2397300Notes

Reaction equation

HRID 2397300 reaction equation
[CH3:1][C:2]([CH:7]=[CH:8][CH2:9][CH:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:3][C:4]([OH:6])=[O:5].[C:18](Cl)(=O)C(Cl)=O.[CH:24]1[CH:29]=[CH:28]C=CC=1>>[CH3:1][C:2]([CH:7]=[CH:8][CH2:9][CH:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:3][C:4]([O:6][CH2:18][CH:29]([CH3:28])[CH3:24])=[O:5]

Participants

4

Reactant 3

HCID 241BenzeneHCID 65578Oxalyl chlorideHCID 1037233,7,11-Trimethyldodeca-2,4-dienoic acid

Product 1

HCID 53880681Isobutyl 3,7,11-trimethyldodeca-2,4-dienoate

Procedure

To a solution of 4.15 g. of 3,7,11-trimethyldodeca-2,4-dienoic acid in 100 ml. of dry benzene, under nitrogen, is added 5.1 ml. of oxalyl chloride. After 2 hours, solvent is removed under reduced pressure and 100 ml. of fresh dry benzene and 6.4 ml. of dry isobutyl alcohol is added. The reaction mixture is concentrated and the concentrate is stirred over 20 g. of activated alumina in pentane for 0.5 hr. and filtered. The filtrate is washed, dried and evaporated under reduced pressure to give isobutyl 3,7,11-trimethyldodeca-2,4-dienoate which can be purified by distillation.

Workup

  1. customsolvent is removed under reduced pressure and 100 ml
  2. additionof dry isobutyl alcohol is added
  3. concentrationThe reaction mixture is concentrated
  4. waitof activated alumina in pentane for 0.5 hr
  5. filtrationand filtered
  6. washThe filtrate is washed
  7. customdried
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7da2645935904472b95f553be7d893d1
Source dataset
uspto-grants-1977_05
Patent number
US04021461

Reaction notes

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