Oxygen → Tert.butyl 2-[5,5-dimethyl-2-oxo-2,3,4,4a,5,6,7,8-octahydronaphth-1-yl]acetate

HRID 36574

반응식

HRID 36574 반응식
C=[C:2]1[CH:7](Cl)[CH2:6][CH2:5][C:4]([CH3:10])([CH3:9])[CH:3]1[CH2:11][CH2:12][C:13](=[O:23])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].O=O.OP([O-])([O-])=O.[K+].[K+]>CO.O.[O-]S([O-])(=O)=O.[Cu+2]>[CH3:10][C:4]1([CH3:9])[CH2:5][CH2:6][CH2:7][C:2]2[CH:3]1[CH2:11][CH2:12][C:13](=[O:23])[C:14]=2[CH2:15][C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17]

참가 물질

7

반응물 3

HCID 977OxygenHCID 24450Potassium Phosphate, Dibasic3회HCID 22362153Tert.butyl 6-(2-methylidene-6,6-dimethyl-3-chlorocyclohex-1-yl)-4-oxo-hexanoate

생성물 1

HCID 67683513Tert.butyl 2-[5,5-dimethyl-2-oxo-2,3,4,4a,5,6,7,8-octahydronaphth-1-yl]acetate수율 52.3%

시약·촉매·용매 3

HCID 24462Copper Sulfate촉매HCID 887Methanol용매HCID 962Water용매2회

실험 절차

190 g (0.55 mol) of tert.butyl 6-(2-methylidene-6,6-dimethyl-3-chlorocyclohex-1-yl)-4-oxo-hexanoate was dissolved in 1.7 l of methanol in a gasification flask, cooled to -70° and ozonized (O2 flow=200 l/h) for 1 hour and 45 minutes. 108 g (1.65 mol) of CuSO4 -activated zinc powder, 200 ml of deionized water and 150 ml of a solution of 115 g of K2HPO4 in 300 ml of H2O was placed in a 4 l four-necked flask fitted with a stirrer, thermometer, condenser and dropping funnel. The cold ozonization mixture was rapidly added dropwise and the resulting grey suspension was heated under reflux. After 17 hours the remainder of the K2HPO4 solution was added and the mixture was heated under reflux. After 4 days the pH value of the mixture was adjusted with saturated K2HPO4 solution to ~7, after 5 days to pH 7.5 and after 6 days to pH 8. After a total of 11 days the grey mixture was left to cool and the phases were separated. The aqueous phase was extracted 3 times with hexane. The combined organic phases were washed neutral 3 times with saturated NaCl solution, dried over MgSO4 and evaporated. 84.17 g of tert.butyl 2-[5,5-dimethyl-2-oxo-2,3,4,4a,5,6,7,8-octahydronaphth-1-yl]acetate was obtained as a yellow oil.

후처리

  1. temperaturecooled to -70°
  2. customfor 1 hour
  3. custom45 minutes
  4. customfitted with a stirrer
  5. customthermometer, condenser and dropping
  6. additionThe cold ozonization mixture was rapidly added dropwise
  7. temperaturethe resulting grey suspension was heated
  8. temperatureunder reflux
  9. temperaturethe mixture was heated
  10. temperatureunder reflux
  11. temperatureto cool
  12. customthe phases were separated
  13. extractionThe aqueous phase was extracted 3 times with hexane
  14. washThe combined organic phases were washed neutral 3 times with saturated NaCl solution
  15. dry with materialdried over MgSO4
  16. customevaporated

출처 및 근거

ORD 기록
ord-7a90d3f620f84bdb96376559c711c394
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05416069

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