Trifluoroacetic acid → HCID 14547226, compound

Participants

Reaction Steps

A solution of the above carbinol (107.8 g) in dichloromethane (540 mL) containing trifluoroacetic acid (21.6 mL) was heated at reflux for 7 hours and then was left at room tempertature overnight. The solution was washed in turn with water (250 mL). 1N NaOH solution (500 mL) and with brine (100 mL). After the aqueous layers were backwashed with dichloromethane (2×100 mL). the combined organic phases were dried (MgSO4) and evaporated to yield 99.2 g of crude (E)-3-(4-methoxyphenyl)-2-octenenitrile as an oil. The crude contained <8% of the (Z)-isomer.

Provenance & Evidence