p-Toluenesulfonic acid monohydrate → N-(4-ethoxycyclohex-3-en-1-yl)acetamide

HRID 225021ノート

反応式

HRID 225021 の反応式
[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]1)(=[O:3])[CH3:2].C([O-])([O-])O[CH2:14][CH3:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][C:8]([O:11][CH2:14][CH3:15])=[CH:7][CH2:6]1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 538565N-(4-Oxocyclohexyl)acetamideHCID 53630039Ethylorthoformate

生成物 1

HCID 15571640N-(4-ethoxycyclohex-3-en-1-yl)acetamide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 6.7 g. of 4-acetamidocyclohexanone [prepared by the method of Fraser and Swingle, Can. J. Chem., 48, 2065 (1970)], in 150 ml. of anhydrous ethanol were added 25 ml. of ethyl orthoformate containing a few crystals of p-toluenesulfonic acid monohydrate. The reaction mixture was stirred at ambient temperature for about 16 hours, after which time the volatile constituents were removed by evaporation in vacuo. The residue comprising the diethylketal was dissolved in 200 ml. of toluene and the toluene was removed by distillation under a nitrogen atmosphere, until all of the diethylketal had been converted to the 1-ethoxycyclohexene derivative. The solution was cooled, washed with aqueous sodium bicarbonate and dried. Evaporation of the toluene yielded a residue comprising 4-acetamido-1-ethoxycyclohexene melting at 100°-102° C. after recrystallization from an ether-hexane solvent mixture; yield=6.2 g.

後処理

  1. customafter which time the volatile constituents were removed by evaporation in vacuo
  2. dissolutionwas dissolved in 200 ml
  3. customof toluene and the toluene was removed by distillation under a nitrogen atmosphere
  4. temperatureThe solution was cooled
  5. washwashed with aqueous sodium bicarbonate
  6. customdried
  7. customEvaporation of the toluene

出典と根拠

ORDレコード
ord-a32404b7363e46f4880991271e7f2c2e
出典データセット
uspto-grants-1980_11
特許番号
US04235776

反応ノート

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