Diethyl Ether → 5,9,13-Trimethyltetradeca-4,6-dien-3-one

HRID 1576590Notes

Reaction equation

HRID 1576590 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.[CH3:18][CH2:19]OCC.C([Li])C.[Cl-].[NH4+]>C1C=CC=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][CH3:19]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 25517Ammonium ChlorideHCID 86734009cis 3,7,11-Trimethyldodeca-2,4-dienoic acidHCID 178506846HCID 178506846, compound

Product 1

HCID 538819695,9,13-Trimethyltetradeca-4,6-dien-3-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3.00 g. of trans/cis 3,7,11-trimethyldodeca-2,4-dienoic acid in 50 ml. ether at 0° under nitrogen is added 28.00 ml. of 0.9 M solution of ethyllithium in benzene. The solution is stirred for 1/2 hour at 0° and then overnight at room temperature. To the reaction mixture is added 50 ml. of ether and the resultant solution is added dropwise with stirring to 300 ml. saturated aqueous ammonium chloride. The organic layer is separated and is washed in turn with 50 ml. saturated aqueous ammonium chloride, 35 ml. water, and 35 ml. saturated aqueous sodium chloride. The solution is dried over calcium sulfate, is concentrated and is then purified by preparative thin layer chromatography (1:3 ether/hexane) and short path distillation (boiling point 100° at .18 mm.) to give 5,9,13-trimethyltetradeca-4,6-dien-3-one (85.4% trans-4, trans-6; 14.6% cis-4, trans-6.).

Workup

  1. customovernight
  2. customat room temperature
  3. additionTo the reaction mixture is added 50 ml
  4. stirringwith stirring to 300 ml
  5. customThe organic layer is separated
  6. washis washed in turn with 50 ml
  7. dry with materialThe solution is dried over calcium sulfate
  8. concentrationis concentrated
  9. distillationis then purified by preparative thin layer chromatography (1:3 ether/hexane) and short path distillation (boiling point 100° at .18 mm.)

Sources & evidence

ORD record
ord-c0dbd2de10f84df3b9c805a76364ba11
Source dataset
uspto-grants-1976_09
Patent number
US03981922

Reaction notes

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