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

HRID 225021

반응식

HRID 225021 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a32404b7363e46f4880991271e7f2c2e
출처 데이터셋
uspto-grants-1980_11
특허 번호
US04235776

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