Reaktion #5661

Reaktionsgleichung

sodium hydroxide

dimethyl malonate

sodium methylate

1-cyclohexylbut-1-en-3-one

butyryl chloride

hydrochloric acid

→

2-butyryl-5-cyclohexylcyclohexane-1,3-dione

Ausbeute 84.1%

Lösungsmittel

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethus obtained
2. 2
   Temperaturcooled to room temperature
3. 3
   workup.STIRRINGthe combined alkaline extracts are stirred for 2 hours at 80° C
4. 4
   Sonstigethe oil obtained
5. 5
   Extraktionis extracted with methylene chloride
6. 6
   Waschenthe extracts are washed with water
7. 7
   Sonstigeevaporated in vacuo

Vorschrift

132 g of dimethyl malonate, 180 g of 30% strength sodium methylate, 152 g of 1-cyclohexylbut-1-en-3-one and 106.5 g of butyryl chloride are reacted in 1 liter of toluene, in a manner similar to that described in Example 1. 5 g of 4-N,N-dimethylaminopyridine are added to the reaction mixture thus obtained and the batch is stirred for 4 hours at 100° C. and then cooled to room temperature. It is then extracted twice with a total of 3.5 moles of sodium hydroxide in 1.5 liters of water and the combined alkaline extracts are stirred for 2 hours at 80° C. They are then acidified with about 270 ml of concentrated hydrochloric acid at 50° C., the oil obtained is extracted with methylene chloride and the extracts are washed with water and evaporated in vacuo. 222 g (84%) of 2-butyryl-5-cyclohexylcyclohexane-1,3-dione are obtained as a pale brown oil.

Quelle