p-Toluenesulfonic acid → HCID 71245667, compound

HRID 628225Notes

Reaction equation

HRID 628225 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.[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]

Participants

6

Reactant 4

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

Product 1

HCID 71245667HCID 71245667, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 21226440Methylenechloride HexaneSolvent

Conditions

Temperature
180 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6150aaac3db646d39d26dbf797a2410c
Source dataset
uspto-grants-2016_04
Patent number
US09312492B2

Reaction notes

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