تفاعل #415691

معادلة التفاعل

p-toluenesulfonic acid monohydrate

acetic anhydride

2-(5-hydroxypentyl)cyclopentanone

acetic anhydride

2-(5-acetoxypentyl)cyclopentanone

2-(5-hydroxypentyl)cyclopentanone 2-(5-acetoxypentyl)-cyclopentanone

→

1-acetoxy-2-(5-acetoxypentyl)-1-cyclopentene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto maintain
2. 2
   workup.DISTILLATIONa steady distillation of acetic acid
3. 3
   أخرىfrom the reaction through a helix-packed fractionation column
4. 4
   درجة الحرارةto maintain a constant volume until complete conversion of starting materials to product
5. 5
   درجة الحرارةThe mixture is cooled
6. 6
   أخرىpartitioned between 2 l
7. 7
   درجة الحرارةof cold water containing solid sodium bicarbonate to maintain a neutral pH
8. 8
   غسيلThe organic phase is washed with saturated brine
9. 9
   تجفيفdried (MgSO4)
10. 10
    أخرىevaporated
11. 11
    أخرىto yield 452 g

الإجراء التجريبي

A solution of 400 g. (2.04 moles) of a mixture of 2-(5-hydroxypentyl)cyclopentanone and 2-(5-acetoxypentyl)cyclopentanone (Example 29) and 4.0 g. of p-toluenesulfonic acid monohydrate in 1 l. of acetic anhydride is refluxed at a rate to maintain a steady distillation of acetic acid from the reaction through a helix-packed fractionation column. The reaction is continued with the addition of acetic anhydride to maintain a constant volume until complete conversion of starting materials to product is evident. The mixture is cooled and partitioned between 2 l. of hexane and 3 l. of cold water containing solid sodium bicarbonate to maintain a neutral pH. The organic phase is washed with saturated brine, dried (MgSO4), and evaporated to yield 452 g. of an oil.

المصدر