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

Participants

Reaction Steps

Concentrated hydrochloric acid (7.8 ml) was added dropwise over 1.5 hour to a mixture of 1-(p-methyl)phenoxy-3-methylbut-2-ene (VI; R=CH2OC6H4.CH3, R1 =R2 =CH3) (12.85 g) and amyl nitrite (11.7 ml) in glacial acetic acid (15.6 ml) at -5° to 0° (ice-salt bath). After a further 1 hour at -5° to 0°, the mixture was filtered. The yellow solid so obtained was washed with acetone and recrystallised from acetone to give the nitrosochloride (V) (7.5 g, yield 42%) as white crystals, m.p. 144°-5° (decomp.).

Provenance & Evidence