Nitric Acid → 1-(1-Methylcyclobutyl)-4-nitrobenzene

HRID 511645

반응식

HRID 511645 반응식
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:9][CH2:8][CH2:7]1.C(OC(=O)C)(=O)C>>[CH3:5][C:6]1([C:10]2[CH:11]=[CH:12][C:13]([N+:1]([O-:4])=[O:2])=[CH:14][CH:15]=2)[CH2:7][CH2:8][CH2:9]1

참가 물질

4

반응물 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 138983(1-Methylcyclobutyl)benzene

생성물 1

HCID 677769921-(1-Methylcyclobutyl)-4-nitrobenzene수율 92.2%

반응 조건

온도
0 °C

실험 절차

70% Nitric acid (7:3, Nitric acid:Water, 0.375 ml, 5.92 mmol) was added dropwise over 60 minutes to a solution of (1-methylcyclobutyl)benzene (346 mg. 2.37 mmol) in Acetic anhydride (1.4 mL, 15 mmol) cooled at 0° C. The temperature of the solution was maintained below 5° C. during the addition. Upon completion of the addition, the reaction was stirred for 60 minutes with cooling. The reaction mixture was poured into 40 ml ice water and the ice was allowed to melt. The aqueous phase was extracted with three×20 ml portions of Et2O and the combined organic phase was washed with 25 ml H2O followed by two 20 ml portions of sat NaHCO3 solution. The organic phase was dried over Na2SO4, filtered and concentrated to yield a light the product as an oil (418 mg) which was used as is in the next step. 1H NMR (400 MHz, CDCl3) d ppm 8.16 (d. J=8.71 Hz, 2H), 7.29 (d, J=8.71 Hz, 2H), 2.41 {m, 2H), 2.15 (m, 3H), 1.88 (m, 1H). 1.48 (s, 3H)

후처리

  1. temperatureThe temperature of the solution was maintained below 5° C. during the addition
  2. additionUpon completion of the addition
  3. temperaturewith cooling
  4. extractionThe aqueous phase was extracted with three×20 ml portions of Et2O
  5. washthe combined organic phase was washed with 25 ml H2O
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-157b919f3e844b0a920e31ebb5d144cb
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096634B2

연결된 노트

불러오는 중…