Water → 6,10,14-Trimethylpentadeca-6,9,13-trien-2-one

HRID 27675Notes

Reaction equation

HRID 27675 reaction equation
C([CH:4]([CH2:10][CH:11]=[C:12]([CH3:19])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])[C:5]([CH3:9])(O)[CH:6]=[CH2:7])(C)=C.CN1C[CH2:24][CH2:23][C:22]1=O.[OH2:27]>>[CH3:9][C:5](=[CH:4][CH2:10][CH:11]=[C:12]([CH3:19])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:17])[CH3:18])[CH2:6][CH2:7][CH2:22][C:23](=[O:27])[CH3:24]

Participants

4

Reactant 3

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 540502533,7,11-Trimethyl-4-(prop-1-EN-2-YL)dodeca-1,6,10-trien-3-OL

Product 1

HCID 539202856,10,14-Trimethylpentadeca-6,9,13-trien-2-oneYield 73%

Conditions

Temperature
190 °C

Procedure

In a nitrogen atmosphere, a mixture of 500 g of 4-isopropenyl-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol (purity 89.61%) and 500 g of N-methylpyrrolidone was heated at 190° C. for 4 hours. The reaction mixture was cooled, poured into a container of water and the resulting aqueous solution was extracted with ether. The ethereal layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulphate. The ethereal extract was distilled under reduced pressure to remove the ether and low-boiling fractions, and the residue was distilled in vacuo to obtain 6,10,14-trimethyl-6,9,13-pentadecatrien-2-one (yield 73%) as a distillate at bp. 121-123° C. / 0.17 mm Hg.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionthe resulting aqueous solution was extracted with ether
  3. washThe ethereal layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulphate
  5. extractionThe ethereal extract
  6. distillationwas distilled under reduced pressure
  7. customto remove the ether and low-boiling fractions
  8. distillationthe residue was distilled in vacuo

Sources & evidence

ORD record
ord-244e19d84405457a9d6966c4eaf816ff
Source dataset
uspto-grants-1980_09
Patent number
US04222963

Reaction notes

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