Water → 12-Methoxy-7,11-dimethyl-3-methylidenedodeca-1,6,10-triene

HRID 437498Notes

Reaction equation

HRID 437498 reaction equation
[CH3:1][O:2][CH2:3][C:4]([CH3:18])=[CH:5][CH2:6][CH2:7][C:8]([CH3:17])=[CH:9][CH2:10][CH2:11][C:12]([CH3:16])(O)[CH:13]=[CH2:14].O.COCC(C)=CCCC(C)=CCC=C(C)C=C>CCOCC.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:1][O:2][CH2:3][C:4]([CH3:18])=[CH:5][CH2:6][CH2:7][C:8]([CH3:17])=[CH:9][CH2:10][CH2:11][C:12](=[CH2:16])[CH:13]=[CH2:14]

Participants

6

Reactant 3

HCID 962WaterHCID 5407294912-Methoxy-3,7,11-trimethyldodeca-1,6,10-trien-3-olHCID 5412246312-Methoxy-3,7,11-trimethyldodeca-1,3,6,10-tetraene

Product 1

HCID 5454062012-Methoxy-7,11-dimethyl-3-methylidenedodeca-1,6,10-trieneYield 47%

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
180 °C

Procedure

5 g of copper sulfate pentahydrate are suspended in 20 g of paraffin oil, with vigorous stirring, and the suspension is heated at 180° C under 20 mm Hg. The water of crystallization which is eliminated is removed through a descending condenser. After the reaction has ended, 25 g (0.1 mole) of 12-methoxy-3,7,11-trimethyl-dodeca-1,6,10-trien-3-ol are added dropwise to the suspension and water and reaction product are distilled off simultaneously (reaction time about 30 minutes). After completion, the distillate is taken up in 100 ml of ether, the ether solution is washed with sodium carbonate solution, then washed neutral with water and dried over sodium sulfate, and the drying agent is then filtered off. After distilling off the ether, the product which remains is fractionated, giving 11 g of a 2:1 mixture of 12-methoxy-3,7,11-trimethyl-dodeca-1,3,6,10-tetraene and 12-methoxy-3-methylene-7,11-dimethyl-dodeca-1,6,10- -triene (yield 47%).

Workup

  1. customThe water of crystallization which
  2. customis eliminated is removed through a descending condenser
  3. distillationare distilled off
  4. customsimultaneously (reaction time about 30 minutes)
  5. washthe ether solution is washed with sodium carbonate solution
  6. washwashed neutral with water
  7. dry with materialdried over sodium sulfate
  8. filtrationthe drying agent is then filtered off
  9. distillationAfter distilling off the ether
  10. customgiving

Sources & evidence

ORD record
ord-b3d9b4c22b5f4837b3606e7263ea68df
Source dataset
uspto-grants-1977_06
Patent number
US04031141

Reaction notes

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