p-Toluenesulfonic acid → HCID 71245667, 화합물

HRID 628225노트

반응식

HRID 628225 반응식
[CH3:1][O:2][C:3]1[C:4]2[S:20][CH:19]=[CH:18][C:5]=2[C:6]2[CH:7]=[C:8]([O:16][CH3:17])[C:9]3[S:15][CH:14]=[CH:13][C:10]=3[C:11]=2[CH:12]=1.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24](S(O)(=O)=O)=[CH:23][CH:22]=1.[CH2:32]([CH:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])CO)[CH2:33][CH2:34][CH3:35].[CH3:45][CH2:46][CH2:47][CH2:48]CC>CCCCCC.ClCCl>[CH2:45]([CH:22]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:21][CH3:31])[CH2:17][O:16][C:8]1[C:9]2[S:15][CH:14]=[CH:13][C:10]=2[C:11]2[CH:12]=[C:3]([O:2][CH2:1][CH:36]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:4]3[S:20][CH:19]=[CH:18][C:5]=3[C:6]=2[CH:7]=1)[CH2:46][CH2:47][CH3:48]

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 8058HexaneHCID 198002-Butyl-1-octanolHCID 71245552HCID 71245552, 화합물

생성물 1

HCID 71245667HCID 71245667, 화합물수율 68.5%

시약·촉매·용매 1

HCID 21226440Methylenechloride Hexane용매

반응 조건

온도
180 °C

실험 절차

5,10-Dimethoxy-1,6-dithia-dicyclopenta[a,f]naphthalene (1.80 g, 6.0 mmol), 1.14 g (6.0 mmol) of toluene-4-sulfonic acid (CH3C6H4SO3H.H2O), and 35 mL of 2-butyloctanol were added into a 250 mL 3-neck flask equipped with a ondenser. The system was heated at 180° C. overnight under argon before the mixture was cooled down to room temperature. Hexane (200 mL) was added and the organic layer was washed with saturated NaHCO3 before the solvent was removed under vacuum. Excess 2-butyloctanol was distilled out under vacuum. Column chromatography (silica gel) with an eluent of hexane/dichloromethane (v/v, 100/4) yielded product 5,10-bis-(2-butyl-octyloxy)-1,6-dithia-dicyclopenta[a,f]naphthalene as a colorless liquid (2.5 g, ˜68.5% yield). 1H NMR (CDCl3, 500 MHz): δ 7.96 (d, 2H, J=5.5 Hz), δ 7.60 (d, 2H, J=5.5 Hz), δ 7.50 (s, 2H), δ 4.23 (d, 4H, J=5.5 Hz), δ 1.99 (m, 2H), δ 1.33 (m, 32H), δ 0.96 (t, 6H, J=7.0 Hz), δ 0.90 (t, 6H, J=7.0 Hz).

후처리

  1. customequipped with a ondenser
  2. temperaturewas cooled down to room temperature
  3. washthe organic layer was washed with saturated NaHCO3 before the solvent
  4. customwas removed under vacuum
  5. distillationExcess 2-butyloctanol was distilled out under vacuum

출처 및 근거

ORD 기록
ord-6150aaac3db646d39d26dbf797a2410c
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09312492B2

반응 노트

불러오는 중…