p-Toluenesulfonic acid → 5,10-Bis-dodecyloxy-1,6-dithia-dicyclopenta[a,f]naphthalene

HRID 575498노트

반응식

HRID 575498 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.C(O)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].[CH3:45][CH2:46][CH2:47][CH2:48]CC>CCCCCC.ClCCl>[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][CH2:45][CH2:46][CH2:47][CH2:48][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:21][CH3:31])[C:4]3[S:20][CH:19]=[CH:18][C:5]=3[C:6]=2[CH:7]=1)[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH3:33]

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 8058HexaneHCID 81931-DodecanolHCID 71245552HCID 71245552, 화합물

생성물 1

HCID 712454095,10-Bis-dodecyloxy-1,6-dithia-dicyclopenta[a,f]naphthalene수율 68.2%

시약·촉매·용매 1

HCID 21226440Methylenechloride Hexane용매

반응 조건

온도
180 °C

실험 절차

5,10-Dimethoxy-1,6-dithia-dicyclopenta[a,f]naphthalene 7 (230 mg, 0.77 mmol) and 145 mg (0.77 mmol) of toluene-4-sulfonic acid (CH3C6H4SO3H.H2O) and 7 mL of 1-dodecanol was added into a 50 mL 3-neck flask equipped with a condenser. The system was heated at 180° C. overnight under argon before it was cooled down to room temperature. Hexane (50 mL) was added and the organic layer was washed with saturated NaHCO3 before the solvent was removed under vacuum. Excess 1-dodecanol was distilled out under vacuum. Column chromatography (silica gel) with the eluent of hexane/dichloromethane (v/v, 4/1) yielded BB-3 as a white solid (320 mg, ˜68.2% yield). 1H NMR (CDCl3, 500 MHz): δ 7.95 (d, 2H, J=5.5 Hz), δ 7.61 (d, 2H, J=5.5 Hz), δ 7.50 (s, 2H), δ 4.35 (t, 4H, J=6.0 Hz), δ 1.99 (m, 4H), δ 1.61 (m, 4H), δ 1.29 (m, 32H), δ 0.90 (t, 6H, J=6.5 Hz).

후처리

  1. customequipped with a condenser
  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 1-dodecanol was distilled out under vacuum

출처 및 근거

ORD 기록
ord-522097fab8fe4c81bec81bd6ab665e17
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09035004B2

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