Reaction #1880955

Reaction equation

water

(2E,7Z)-1,1-dimethoxy-2,4,7-decatriene

→

(2E,7Z)-2,4,7-decatrienal

Yield 96.0%

Solvents

acetone

Et2O

Conditions

Workup

1. 1
   workup.ADDITIONwere added 0.2 g of AMBERLITE®
2. 2
   Otherthe reaction mixture so obtained
3. 3
   FiltrationAfterwards, the reaction mixture was filtered
4. 4
   Concentrationconcentrated
5. 5
   OtherThe crude product thus obtained
6. 6
   Washthe organic phase has been washed twice with brine
7. 7
   Dryingdried over Na2SO4
8. 8
   Concentrationconcentrated
9. 9
   Otherto yield 8.8 g of an extract
10. 10
    workup.DISTILLATIONThe extract has been further purified by distillation over a Vigreux column (52–54° C./0.1 mbar)

Procedure

To a solution of 9.8 g of a mixture of (2E,7Z)-1,1-dimethoxy-2,4,7-decatriene as obtained in example 1 (50 mmoles) and 2.7 ml of water (150 mmoles) in 150 ml of acetone were added 0.2 g of AMBERLITE®, and the reaction mixture so obtained was stirred for 1 hour at room temperature. Afterwards, the reaction mixture was filtered and neutralized with 1 ml of a saturated aqueous solution of NaHCO3, and then concentrated. The crude product thus obtained was dissolved in Et2O and the organic phase has been washed twice with brine, dried over Na2SO4 and concentrated to yield 8.8 g of an extract. The extract has been further purified by distillation over a Vigreux column (52–54° C./0.1 mbar) to yield 7.2 g of a mixture of (2E,7Z)-2,4,7-decatrienal (4Z:4E=88:8)(purity=96%, yield=96%). The product thus obtained had the same spectroscopic data as described in WO 01/58282.

Source