Ammonia → 1-Methoxy-4-(4-hydroxybutyl)cyclohexa-1,4-diene

Participants

Reaction Steps

Ammonia (75 mL) is liquified in a flask at -40° and a solution of 5 g (28 mmol) of p-(4-hydroxybutyl)anisole in 25 mL ethanol is added. 2.76 g (0.12 mmol) of sodium is added in small pieces over 1 hour. The blue solution is then stirred at -40° for 10 minutes during which time the solution decolorizes with the formation of a white precipitate. The reaction is quenched using 5.88 g solid ammonium chloride followed by 25 mL water. The solvent is evaporated under a stream of nitrogen and then poured into brine and extracted with ether (4×100 mL). The organic extracts are combined, dried, filtered and subjected to evaporation to give 1-methoxy-4-(4-hydroxybutyl)cyclohexa1,4-diene as an oil.

Provenance & Evidence