Reaktion #312250

Reaktionsgleichung

water

1-octyn-4-ol

benzoyl chloride

acetylene

→

4-benzoyloxy-1-octyne

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITto stand for 15 minutes
2. 2
   Einengenconcentrated
3. 3
   WaschenA solution of the residue in ether is washed successively with ice-cold hydrochloric acid, water, sodium bicarbonate solution, and brine
4. 4
   TrocknenThe solution is dried over magnesium sulfate
5. 5
   Filtrationfiltered through Celite
6. 6
   Einengenconcentrated
7. 7
   Sonstigeto give an oil, λ max

Vorschrift

To a stirred solution of 63. g (0.50 moles) of 1-octyn-4-ol (Example 93) in 500 ml of pyridine is added 77 g (0.55 moles) of benzoyl chloride. After stirring for 1.5 hours the mixture is treated with 10 ml of water, allowed to stand for 15 minutes, and concentrated. A solution of the residue in ether is washed successively with ice-cold hydrochloric acid, water, sodium bicarbonate solution, and brine. The solution is dried over magnesium sulfate, filtered through Celite, and concentrated to give an oil, λ max. 3240 (terminal acetylene) and 1730 cm-1 (benzyloxy group).

Quelle