Hydroquinone → 4-Methoxybicyclo[2.2.2]octan-2-one

HRID 259353

반응식

HRID 259353 반응식
C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C=CC(O)=CC=1)O.[C:20]([CH:23]1[CH2:28][CH2:27][C:26]([O:29][CH3:30])=[CH:25][CH2:24]1)(=[O:22])[CH3:21].C[O-].[Na+]>C1C=CC=CC=1.O>[CH3:30][O:29][C:26]12[CH2:27][CH2:28][CH:23]([CH2:24][CH2:25]1)[C:20](=[O:22])[CH2:21]2

참가 물질

7

반응물 4

HCID 785HydroquinoneHCID 6101p-Toluenesulfonic acidHCID 10942334Sodium MethoxideHCID 203422181-Acetyl-4-methoxy-3-cyclohexene

생성물 1

HCID 5663034-Methoxybicyclo[2.2.2]octan-2-one

시약·촉매·용매 2

HCID 241Benzene용매2회HCID 962Water용매

실험 절차

A mixture of 13.2 g. of p-toluenesulfonic acid and 0.9 g. of hydroquinone in 540 ml. of benzene was heated at reflux under a Dean Stark trap until no more water was evolved. A solution of 90.6 g. of 1-Acetyl-4-methoxy-3-cyclohexene in 750 ml. of benzene was then added to the refluxing solution over 6 hrs. Following an additional hr's heating the mixture was cooled and treated with 16 ml. of 4.64 N methanolic sodium methoxide. The mixture was washed twice with water and the solvent evaporated in vacuum. The residual oil was distilled at 0.45 mm to afford 64.2 g. of bicyclic ketone 4-Methoxybicyclo[2,2,2]-octan-2-one, bp 77°-82°.

후처리

  1. additionA mixture of 13.2 g
  2. temperatureheating the mixture
  3. temperaturewas cooled
  4. additiontreated with 16 ml
  5. washThe mixture was washed twice with water
  6. customthe solvent evaporated in vacuum
  7. distillationThe residual oil was distilled at 0.45 mm
  8. customto afford 64.2 g

출처 및 근거

ORD 기록
ord-29ea36d01e00401692aba3af066ec3ac
출처 데이터셋
uspto-grants-1977_07
특허 번호
US04036977

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