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

HRID 575498Notes

Reaction equation

HRID 575498 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 21226440Methylenechloride HexaneSolvent

Conditions

Temperature
180 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-522097fab8fe4c81bec81bd6ab665e17
Source dataset
uspto-grants-2015_05
Patent number
US09035004B2

Reaction notes

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