Hydrochloric Acid → 2-Butyryl-5-cyclohexylcyclohexane-1,3-dione

HRID 5565

反応式

HRID 5565 の反応式
C(OC)(=O)[CH2:2][C:3](OC)=[O:4].C[O-].[Na+].[CH:13]1([CH:19]=[CH:20][C:21](=[O:23])[CH3:22])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[C:24](Cl)(=[O:28])[CH2:25][CH2:26][CH3:27].[OH-].[Na+].Cl>C1(C)C=CC=CC=1.O>[C:24]([CH:22]1[C:21](=[O:23])[CH2:20][CH:19]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:2][C:3]1=[O:4])(=[O:28])[CH2:25][CH2:26][CH3:27]

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 7943Dimethyl malonateHCID 8855Butyryl chlorideHCID 14798Sodium HydroxideHCID 955971-Cyclohexylbut-1-en-3-oneHCID 10942334Sodium Methoxide

生成物 1

HCID 197965792-Butyryl-5-cyclohexylcyclohexane-1,3-dione収率 84.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  1. customthus obtained
  2. temperaturecooled to room temperature
  3. stirringthe combined alkaline extracts are stirred for 2 hours at 80° C
  4. customthe oil obtained
  5. extractionis extracted with methylene chloride
  6. washthe extracts are washed with water
  7. customevaporated in vacuo

出典と根拠

ORDレコード
ord-c5320739ecb94875895071e346290d87
出典データセット
uspto-grants-1993_09
特許番号
US05245041

関連ノート

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