Toluene → 2,6-Di(propan-2-yl)-4-(prop-2-en-1-yl)aniline

HRID 2250975

반응식

HRID 2250975 반응식
C([NH:4][C:5]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][CH:8]=[CH:7][C:6]=1[CH:14]([CH3:16])[CH3:15])C=C.[OH-].[Na+].[C:19]1(C)[CH:24]=CC=C[CH:20]=1>[Cl-].[Cl-].[Zn+2]>[CH2:24]([C:8]1[CH:7]=[C:6]([CH:14]([CH3:15])[CH3:16])[C:5]([NH2:4])=[C:10]([CH:11]([CH3:12])[CH3:13])[CH:9]=1)[CH:19]=[CH2:20]

참가 물질

5

반응물 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 713595712,6-Di(propan-2-yl)-N-(prop-2-en-1-yl)aniline

생성물 1

HCID 219306712,6-Di(propan-2-yl)-4-(prop-2-en-1-yl)aniline수율 70.9%

시약·촉매·용매 1

HCID 3007855Zincchloride촉매

실험 절차

N-allyl-2,6-diisopropyl aniline (18.33 g, 0.084 mol) and ZnCl2 (13.6 g, 0.1 mol) were added to a 100 ml toluene solution. This solution was refluxed for 5 hr and then poured into a NaOH aqueous solution. Extraction with Et2O (3×50 ml) and distillation (79.93 Pa, 98° C.) yielded 13.0 g (70.9%) of 4-allyl-2,6-diisopropyl aniline. Nd30=1.5340, 1H-NMR (ppm,CDCl3): δ=6.85(s, 2H, Ph-Hm),5.98(m, 1H, CH═C),5.09(d, 1H, C═C—Htrans),5.03(d, 1H, C═C—Hcis),3.6(br, 2H, NH2), 3.30(d, 2H, CH2—C═C), 2.92(m, 2H, CH(Me)2), 1.26(d, 12H, C(CH3)2)

후처리

  1. temperatureThis solution was refluxed for 5 hr
  2. extractionExtraction
  3. distillationwith Et2O (3×50 ml) and distillation (79.93 Pa, 98° C.)

출처 및 근거

ORD 기록
ord-37dd3eed3ab64d15b14db251eb2e7a4a
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07319083B2

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