Lithium Hydroxide → 3,5-Didecanyldithieno[3,2-b:2',3'-d]thiophene-2,6-dicarboxylic acid

HRID 83963Notes

Reaction equation

HRID 83963 reaction equation
[CH2:1]([C:11]1[C:18]2[S:17][C:16]3[C:19]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[C:20]([C:22]([O:24]CC)=[O:23])[S:21][C:15]=3[C:14]=2[S:13][C:12]=1[C:37]([O:39]CC)=[O:38])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[Li+].[OH-].C1COCC1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CO>[CH2:27]([C:19]1[C:16]2[S:17][C:18]3[C:11]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[C:12]([C:37]([OH:39])=[O:38])[S:13][C:14]=3[C:15]=2[S:21][C:20]=1[C:22]([OH:24])=[O:23])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 16103487HCID 16103487, compound

Product 1

HCID 161034573,5-Didecanyldithieno[3,2-b:2',3'-d]thiophene-2,6-dicarboxylic acidYield 98%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 887MethanolSolvent

Procedure

Compound 67 (10.2 g, 0.017 mol) is mixed with LiOH (1.0 g in 10 mL water), THF (100 mL), MeOH (20 mL) and a catalytic amount (−35 mg) of tetrabutylammonium iodide. This mixture is heated at reflux overnight, then most of the solvent is evaporated. The residue is acidified with concentrated HCl (30 mL), forming a solid which is collected by filtration, washed thoroughly with water, and vacuum dried to yield compound 68 (8.6 g, 98% yield). M.P.: 280.1° C. 1H NMR (CD2Cl2): δ 3.24 (t, 4H), 1.72 (m, 2H), 1.29 (m, 30H), 0.88 (t, 6H). 13C NMR: 168.46, 148.24, 146.58, 136.32, 35.91, 33.64, 28.91 (m, overlap), 26.60, 17.49.

Workup

  1. temperatureThis mixture is heated
  2. temperatureat reflux overnight
  3. custommost of the solvent is evaporated
  4. customforming a solid which
  5. filtrationis collected by filtration
  6. washwashed thoroughly with water, and vacuum
  7. customdried

Sources & evidence

ORD record
ord-aa72ae07ff9644fc960844363769874a
Source dataset
uspto-grants-2014_09
Patent number
US08846855B2

Reaction notes

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