Methanol → E-5-Decen-1-ol

Participants

Reaction Steps

A portion of the acetate is removed and converted to the corresponding alcohol as follows. 15.0 g (67 mmol) of the 5-decenyl acetate, 35 mL of methanol and 34 mL of 2 M sodium hydroxide were added to a 250 mL round-bottomed flask. This mixture was stirred for 3 hours at room temperature. After 3 hours the hydrolysis was complete, 10 mL of hexane was added and the solution was washed with 10 mL of 1 M HCl, 10 mL of NaHCO3 -saturated water and 10 mL of brine. The organic phase was dried with sodium sulfate, filtered and the hexane removed under reduced pressure to yield 9.4 g of 5-decenol. GC analysis showed the isometric ratio to be 80:20 E:Z.

Provenance & Evidence