Water → HCID 54549204, compound

HRID 1975631Notes

Reaction equation

HRID 1975631 reaction equation
[OH-].[Na+].O.[CH3:4][C:5](=[CH:9][CH2:10][CH:11]1[CH2:15][CH2:14][CH:13]([CH3:16])[C:12]1([CH3:18])[CH3:17])[C:6](=[O:8])[CH3:7].[CH3:19]Cl>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1(C)C=CC=CC=1>[CH3:4][C:5]([CH3:19])([CH:9]=[CH:10][CH:11]1[CH2:15][CH2:14][CH:13]([CH3:16])[C:12]1([CH3:17])[CH3:18])[C:6](=[O:8])[CH3:7]

Participants

7

Reactant 4

HCID 962WaterHCID 6327Methyl ChlorideHCID 14798Sodium HydroxideHCID 537486543-Methyl-5-(2,2,3-trimethylcyclopentyl)pent-3-en-2-one

Product 1

HCID 54549204HCID 54549204, compound

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

To a rapidly stirred mixture of 400 g of NaOH, 400 g of H2O and 400 ml of toluene are added 8 g of tricaprylmethylammonium chloride (Aliquat 336), then 70 g of 3-methyl-5-(2,2,3-trimethyl-cyclopent-1-yl)-pent-3-en-2-one (0.34 moles) at room temperature. At the end of the addition methyl chloride is injected over~20 hours. The temperature reaches 30° C. The reaction is monitored by GC. After 20 hours the alkylation is finished and the reaction mass is poured into ice. The resulting mixture is extracted with ether. The organic phase is washed with H2O and the solvents are removed by evaporation. The distillation of the crude product using a Widmer column leads to 38 g of pure ketone (purity: 96%, GC).

Workup

  1. customat room temperature
  2. customreaches 30° C
  3. waitAfter 20 hours the alkylation is finished
  4. additionthe reaction mass is poured into ice
  5. extractionThe resulting mixture is extracted with ether
  6. washThe organic phase is washed with H2O
  7. customthe solvents are removed by evaporation
  8. distillationThe distillation of the crude product

Sources & evidence

ORD record
ord-ca5aa2c53ee14906bee3268d25c97560
Source dataset
uspto-grants-1994_02
Patent number
US05288701

Reaction notes

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