3-ethylpent-2-en-1-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Cyclohexylidene ethanol (VI) (23 g) was dissolved in glacial acetic acid (76 ml). Amyl nitrite (21.5 g) was added and the mixture was cooled in an ice-salt bath. The cooled solution was treated dropwise with cold concentrated hydrochloric acid (23 ml) with stirring. After the addition of the acid was complete the reaction mixture was stirred at the same temperature for 30 min, followed by cooling in an acetone-carbon dioxide bath for 10 min. The buff-coloured solid was filtered off, washed with cold methanol and recrystallised from acetone to give the nitrosochloride (V) (15 g; yield 43%) as colourless needles, m.p. 130°. the mixture was cooled in an ice-salt bath After the addition of the acid was stirred at the same temperature for 30 min by cooling in an acetone-carbon dioxide bath for 10 min The buff-coloured solid was filtered off washed with cold methanol recrystallised from acetone

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Cyclohexylidene ethanol (VI) (23 g) was dissolved in glacial acetic acid (76 ml). Amyl nitrite (21.5 g) was added and the mixture was cooled in an ice-salt bath. The cooled solution was treated dropwise with cold concentrated hydrochloric acid (23 ml) with stirring. After the addition of the acid was complete the reaction mixture was stirred at the same temperature for 30 min, followed by cooling in an acetone-carbon dioxide bath for 10 min. The buff-coloured solid was filtered off, washed with cold methanol and recrystallised from acetone to give the nitrosochloride (V) (15 g; yield 43%) as colourless needles, m.p. 130°. the mixture was cooled in an ice-salt bath After the addition of the acid was stirred at the same temperature for 30 min by cooling in an acetone-carbon dioxide bath for 10 min The buff-coloured solid was filtered off washed with cold methanol recrystallised from acetone

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Cyclohexylidene ethanol (VI) (23 g) was dissolved in glacial acetic acid (76 ml). Amyl nitrite (21.5 g) was added and the mixture was cooled in an ice-salt bath. The cooled solution was treated dropwise with cold concentrated hydrochloric acid (23 ml) with stirring. After the addition of the acid was complete the reaction mixture was stirred at the same temperature for 30 min, followed by cooling in an acetone-carbon dioxide bath for 10 min. The buff-coloured solid was filtered off, washed with cold methanol and recrystallised from acetone to give the nitrosochloride (V) (15 g; yield 43%) as colourless needles, m.p. 130°. the mixture was cooled in an ice-salt bath After the addition of the acid was stirred at the same temperature for 30 min by cooling in an acetone-carbon dioxide bath for 10 min The buff-coloured solid was filtered off washed with cold methanol recrystallised from acetone