Acetic Acid → 1-[4-(3,3,5,5-Tetramethylcyclohexyl)phenyl]ethanone

HRID 1071917노트

반응식

HRID 1071917 반응식
Cl[Si](C)(C)C.O[C:7]1([C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=2)[CH2:12][C:11]([CH3:14])([CH3:13])[CH2:10][C:9]([CH3:16])([CH3:15])[CH2:8]1.[I-].[Na+].C(O)(=O)C>C(#N)C.[Zn]>[CH3:13][C:11]1([CH3:14])[CH2:10][C:9]([CH3:15])([CH3:16])[CH2:8][CH:7]([C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=2)[CH2:12]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 223904201-[4-(Hydroxy-3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone

생성물 1

HCID 223904281-[4-(3,3,5,5-Tetramethylcyclohexyl)phenyl]ethanone수율 68%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 6342Acetonitrile용매2회

실험 절차

38.1 ml of chlorotrimethylsilane are added over 45 minutes to a solution of 40.45 g of 1-[4-(hydroxy-3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone (compound V′.1) and 56.21 g of sodium iodide in 230 ml of anhydrous acetonitrile. During the addition, the temperature is maintained between 35° C. and 40° C. After stirring for 2 hours, 40 ml of acetonitrile and 39.4 ml of acetic acid are added. Next, 29.4 g of finely powdered zinc are added portionwise with stirring and at room temperature. The reaction mixture is refluxed with vigorous stirring for 4 hours. After cooling to room temperature, the reaction medium is filtered through Celite and then washed with saturated aqueous sodium bicarbonate solution. The organic phase is concentrated under reduced pressure and the oil obtained is purified by chromatography on a column of silica gel, eluting with a 95/5 (v/v) cyclohexane/ethyl acetate mixture; yield=68% ; m.p.=54° C. The following compounds are obtained in the same way:

후처리

  1. additionDuring the addition
  2. temperaturethe temperature is maintained between 35° C. and 40° C
  3. stirringwith stirring and at room temperature
  4. temperatureThe reaction mixture is refluxed
  5. stirringwith vigorous stirring for 4 hours
  6. filtrationthe reaction medium is filtered through Celite
  7. washwashed with saturated aqueous sodium bicarbonate solution
  8. concentrationThe organic phase is concentrated under reduced pressure
  9. customthe oil obtained
  10. customis purified by chromatography on a column of silica gel
  11. washeluting with a 95/5 (v/v) cyclohexane/ethyl acetate mixture
  12. customThe following compounds are obtained in the same way

출처 및 근거

ORD 기록
ord-bcc95865f78244be8ee353f2f4406c36
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06908914B1

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