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

HRID 259353

反応式

HRID 259353 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 241Benzene溶媒2 回HCID 962Water溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-29ea36d01e00401692aba3af066ec3ac
出典データセット
uspto-grants-1977_07
特許番号
US04036977

関連ノート

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