Hydrochloric Acid → (3-Chloro-3-methyl-2-nitrosobutoxy)benzene

Participants

Reaction Steps

Concentrated hydrochloric acid (8.1 ml) was added dropwise over 10 minutes to a mixture of 1-(p-methoxy)phenoxy-3-methylbut-2-ene (VI; R=CH2OC6H4.OCH3, R1 =R2 =CH3) (16.05 g) and amyl nitrite (12.1 ml) in glacial acetic acid (16.2 ml) at -5° to 0° (ice-salt bath). After a further 1 hour at -5° to 0°, the mixture was filtered. The solid so obtained was washed with acetone and recrystallised from acetone to give the nitrosochloride (V) (4.87 g, yield 22%) as pale yellow crystals, m.p. 123° (decomp.).

Provenance & Evidence