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

HRID 1446783

반응식

HRID 1446783 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 94%

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% 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-35bc80ab15be4079989d30cb1481f97c
출처 데이터셋
uspto-grants-1982_02
특허 번호
US04313856

연결된 노트

불러오는 중…