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

HRID 223289

반응식

HRID 223289 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-378c727ab75b4e24a70522e6edb0de92
출처 데이터셋
uspto-grants-1982_10
특허 번호
US04352943

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