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

Reaction equation

N.[OH:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.[Na]>C(O)C>[CH3:14][O:13][C:10]1[CH2:11][CH:12]=[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][OH:2])[CH2:8][CH:9]=1

Participants

Procedure

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.