Chloride → HCID 54345317, compound

HRID 1381324Notes

Reaction equation

HRID 1381324 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[C:4]([CH:10]=[CH:11][C:12]([CH3:16])([OH:15])[CH:13]=[CH2:14])=[C:3]1[CH3:17].[Cl-].[OH-].[K+].S(OC)(O[CH3:25])(=O)=O>CCCCCC.C(OCC)C.CCCCCCCC(OCC(OC(CCCCCCC)=O)COC(CCCCCCC)=O)=O>[O:1]=[C:2]1[CH2:7][CH2:6][C:5]([CH3:8])([CH3:9])[C:4]([CH:10]=[CH:11][C:12]([O:15][CH3:25])([CH3:16])[CH:13]=[CH2:14])=[C:3]1[CH3:17]

Participants

8

Reactant 4

HCID 312ChlorideHCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 54402789HCID 54402789, compound

Product 1

HCID 54345317HCID 54345317, compoundYield 99.6%

Reagents, catalysts & solvents 3

HCID 10850TricaprylinCatalystHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

2.34 g of 1-(3-oxo-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-1,4-pentadien-3-ol were dissolved in 15 ml of hexane and 5 ml of diethyl ether, treated with 2 drops of tricaprylm thylammonium chloride and 4.54 ml of aqueous potassium hydroxide solution (prepared from 70 g of powdered potassium hydroxide and 50 ml of water) and stirred well. 1.98 g of dimethyl sulphate were subsequently added to the mixture and the course of the reaction was followed by gas chromatography. After stirring at room temperature for 4 hours (product/educt ratio 99.7:0.3), the mixture was poured on to ice. The organic phase was separated, washed neutral with water, dried over sodium sulphate and concentrated under a water-jet vacuum. There were obtained 2.47 g of 1-(3-oxo-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methoxy-3-methyl-1,4-pentadiene as a yellow oil.

Workup

  1. stirringAfter stirring at room temperature for 4 hours (product/educt ratio 99.7:0.3)
  2. additionthe mixture was poured on to ice
  3. customThe organic phase was separated
  4. washwashed neutral with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under a water-jet vacuum

Sources & evidence

ORD record
ord-ee81bfd602894e43bb23b5a60584539e
Source dataset
uspto-grants-1986_04
Patent number
US04585885

Reaction notes

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