Реакция #524237

Уравнение реакции

sodium hydroxide

Allyl bromide

cyclohexanedione

potassium hydroxide

→

2-Allyl-1,3-cyclohexanedione

Растворители

ethyl acetate

Условия реакции

Обработка

1. 1
   workup.ADDITIONthe reaction was mixed with 1500 ml
2. 2
   Фильтрацияof ethyl ether, filtered
3. 3
   ДругоеA brown solid (188 g.) formed upon refrigeration at 0° C
4. 4
   Промывкаthe solution was washed with water (3× 150 ml.)
5. 5
   Сушкаdried (MgSO4)
6. 6
   workup.ADDITIONtreated with charcoal, and condensed until turbid
7. 7
   ТемператураUpon cooling
8. 8
   Другое(57%) of 2-allyl-1,3-cyclohexanedione was collected

Методика

Allyl bromide (195 g., 1.62 mol.) was added over a 15 minute period to a stirred ice-cold mixture of cyclohexanedione (165 g., 1.47 mol.), copper-bronze (4.5 g.), and 330 ml. of 20% by weight aqueous potassium hydroxide. After 6 hours, the reaction was mixed with 1500 ml. of a 5% by weight aqueous sodium hydroxide solution and 1000 ml. of ethyl ether, filtered and the separated water layer acidified with 4 N aqueous hydrochloric acid to pH 1. A brown solid (188 g.) formed upon refrigeration at 0° C. The solid was taken up in ethyl acetate and the solution was washed with water (3× 150 ml.), dried (MgSO4), treated with charcoal, and condensed until turbid. Upon cooling, 126 g. (57%) of 2-allyl-1,3-cyclohexanedione was collected, m.p. 125°-127° C.

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