Hydrochloric Acid → Non-3-ene

Temperature

37.5 °C

To a dry 2 L multi-neck round bottom flask fitted with an air stirrer, nitrogen inlet condenser and an additional funnel, 400 ml of THF, 44 g of NaH, and 21.2 g of dihydroethyl linalool were added and heated to 35-40° C. 170 g of dihydrolinalool g was then added to the reaction mixture dropwise over 2 hours. The mixture was aged for 8 hours. 9 g of HMPA (available from Aldrich Chemical Company) was added and the mixture was stirred. 144 g of CH3I was added dropwise to the reaction mixture, further aged for two hours and then sampled hourly until maximum conversion was reached. The mixture was cooled and 800 ml of 5% HCl solution was added, allowed to settle, and the organic layer was separated. The aqueous layer was extracted with 3×100 ml of toluene and then dried over MgSO4 to provide 3-nonene, 7-methoxy-3,7-dimethyl-.

1. customTo a dry 2 L multi-neck round bottom flask fitted with an air stirrer, nitrogen inlet condenser and an additional funnel
2. aliquotsampled hourly until maximum conversion
3. temperatureThe mixture was cooled
4. customthe organic layer was separated
5. extractionThe aqueous layer was extracted with 3×100 ml of toluene
6. dry with materialdried over MgSO4

ORD record

ord-b33b965f836d448d8aebd9d35a55d478

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07531489B2