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

HRID 575498ノート

反応式

HRID 575498 の反応式
[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]

参加物

6

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 8058HexaneHCID 81931-DodecanolHCID 71245552HCID 71245552、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 21226440Methylenechloride Hexane溶媒

反応条件

温度
180 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-522097fab8fe4c81bec81bd6ab665e17
出典データセット
uspto-grants-2015_05
特許番号
US09035004B2

反応ノート

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