Sulfuric Acid → 3-(3-Oxobut-1-enyl)-2,4,4-trimethylcyclohex-2-en-1-one

HRID 1106093

反応式

HRID 1106093 の反応式
[CH3:1][C:2]1[CH:7]([OH:8])[CH2:6][CH2:5][C:4]([CH3:10])([CH3:9])[C:3]=1[CH:11]=[CH:12][C:13](=[O:15])[CH3:14].O.O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].S(=O)(=O)(O)O>CCOCC>[CH3:1][C:2]1[C:7](=[O:8])[CH2:6][CH2:5][C:4]([CH3:9])([CH3:10])[C:3]=1[CH:11]=[CH:12][C:13](=[O:15])[CH3:14]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 108005Sodium dichromate dihydrateHCID 540347274-(3-Hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one

生成物 1

HCID 337363-(3-Oxobut-1-enyl)-2,4,4-trimethylcyclohex-2-en-1-one収率 734.3%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
5 °C

実験手順

To a solution, pre-cooled to 0° C., of 140 g (0.068 mol) of 4-(2,6,6-trimethyl-3-hydroxy-cyclohex-1-en-1-yl)-but-3-en-2-one in 500 ml of ether are added dropwise over a period of 10 minutes 700 ml of an aqueous solution, cooled to 0° C., of 202.6 g of sodium dichromate dihydrate and 186 g of concentrated sulphuric acid with intensive cooling and good stirring so that a temperature of 5° C. is not exceeded. The mixture is then stirred for a further 5 minutes at 5° C., treated with 500 ml of ether, the ether phase is washed three times with water, three times with soda solution and again three times with water, dried over sodium sulphate and concentrated. Distillation of the resulting 125 g of crude product over a 10 cm Widmer column gave 103 g of more than 94% pure 4-(2,6,6-trimethyl-3-oxo-cyclohex-1-en-1-yl)-but- 3-en-2-one of boiling point 109°-110° C./0.05 mm Hg; melting point 50°-51° C.

後処理

  1. temperaturewith intensive cooling
  2. stirringThe mixture is then stirred for a further 5 minutes at 5° C.
  3. washthe ether phase is washed three times with water, three times with soda solution and again three times with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. distillationDistillation of the resulting 125 g of crude product over a 10 cm Widmer column

出典と根拠

ORDレコード
ord-f6f2645b82d4426cbf7dd5593ee9b3f5
出典データセット
uspto-grants-1982_01
特許番号
US04311718

関連ノート

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