Reaction #93928

Reaction equation

ether

1-Ethynylcyclohexan-1-ol

acetic anhydride

sulfuric acid

1-acetoxy-1-ethynylcyclohexane

→

8-methylsulfonyl-11-(1-hydroxycyclohexyl)-10-undecynoic acid

Conditions

Workup

1. 1
   workup.ADDITIONThe temperature of the reaction mixture is kept at 10°-12° C. during the addition by means of an ice bath
2. 2
   Temperaturewithout cooling for 1.5 hours
3. 3
   workup.ADDITIONIt is then poured into 300 ml
4. 4
   Washwashed with water, dilute sodium bicarbonate solution and brine
5. 5
   Dryingdried over sodium sulfate
6. 6
   workup.DISTILLATIONDistillation
7. 7
   Otheraffords 107 g

Procedure

1-Ethynylcyclohexan-1-ol(100 g., 0.8 mole) is added dropwise with stirring to a mixture of acetic anhydride (86.7 g., 0.85 mole) and sulfuric acid (0.25 ml.). The temperature of the reaction mixture is kept at 10°-12° C. during the addition by means of an ice bath. The mixture is then stirred without cooling for 1.5 hours. It is then poured into 300 ml. of ice water. The oily product is taken up in ether, washed with water, dilute sodium bicarbonate solution and brine and dried over sodium sulfate. Distillation affords 107 g. (80%) of 1-acetoxy-1-ethynylcyclohexane, b.p. 95°-97° C./15 mm.

Source