1-Dodecanol → 4,9-Bis(dodecyloxy)naphtho[1,2-b:5,6-b']dithiophene

HRID 575495Notes

Reaction equation

HRID 575495 reaction equation
[CH3:1][O:2][C:3]1[C:18]2[C:14]3[S:15][CH:16]=[CH:17][C:13]=3[CH:12]=[C:11]([O:19][CH3:20])[C:10]=2[C:6]2[S:7][CH:8]=[CH:9][C:5]=2[CH:4]=1.O.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25](S(O)(=O)=O)=[CH:24][CH:23]=1.C(O)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]>>[CH2:20]([O:19][C:11]1[C:10]2[C:6]3[S:7][CH:8]=[CH:9][C:5]=3[CH:4]=[C:3]([O:2][CH2:1][CH2:18][CH2:3][CH2:4][CH2:5][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:22][CH3:32])[C:18]=2[C:14]2[S:15][CH:16]=[CH:17][C:13]=2[CH:12]=1)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH3:34]

Participants

4

Reactant 3

HCID 81931-DodecanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 712456764,9-Dimethoxynaphtho[1,2-b:5,6-b']dithiophene

Product 1

HCID 712455044,9-Bis(dodecyloxy)naphtho[1,2-b:5,6-b']dithiopheneYield 225.8%

Procedure

Compound 4 (150 mg, 0.50 mmol) and p-toluenesulfonic acid monohydrate (15.2 mg, 0.080 mmol) were heated in dodecan-1-ol (3.7 g, 20 mmol) at 200° C. under nitrogen overnight. Upon cooling down to room temperature, the solvent was removed under vacuum and the residual was purified with silica gel column and eluted with CHCl3/hexane (1:4 and then 2:3) to give compound BB1 as a white solid (110 mg, about 36% yield). 1H NMR (500 MHz, CDCl3): δ 7.56 (d, J=5.0 Hz, 2H), 7.42 (d, J=5.0 Hz, 2H), 7.41 (s, 2H), 4.32 (t, J=6.5 Hz, 4H), 2.13 (quintet, J=7.5 Hz, 4H); 1.68 (quintet, J=7.5 Hz, 4H); 1.39 (m, 32H); 0.86 (t, J=6.0 Hz, 6H).

Workup

  1. customthe solvent was removed under vacuum
  2. customthe residual was purified with silica gel column
  3. washeluted with CHCl3/hexane (1:4

Sources & evidence

ORD record
ord-e17a923a896c4df0883d9943706b198d
Source dataset
uspto-grants-2015_05
Patent number
US09035004B2

Reaction notes

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