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Sodium Hydroxide → 4,8-Bis(octyloxy)benzo[1,2-b:4,5-b']dithiophene

HRID 2090128
Notes
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Reaction equation

HRID 2090128 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:14])[C:7]3[S:8][CH:9]=[CH:10][C:11]=3[C:12](=[O:13])[C:2]1=2.[OH-].[Na+].C1(C)C=CC(S(O[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])(=O)=O)=CC=1>[Zn].C(O)C>[CH2:5]([O:14][C:6]1[C:7]2[S:8][CH:9]=[CH:10][C:11]=2[C:12]([O:13][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH3:27])=[C:2]2[S:1][CH:5]=[CH:4][C:3]=12)[CH2:4][CH2:3][CH2:2][CH2:12][CH2:11][CH2:7][CH3:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 288478(Benzo(1,2-b:4,5-b)dithiophene-4,8-dione)HCID 599296n-Octyl p-Toluenesulfonate

Product 1

HCID 582808994,8-Bis(octyloxy)benzo[1,2-b:4,5-b']dithiopheneYield 62%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst
HCID 702
Ethanol
Solvent

Procedure

1.0 g (4.5 mmol) of benzo[1,2-b:4,5-b′]dithiophene-4,8-dione was mixed with 0.65 g (10 mmol) of zinc dust in a flask. Then, 4 ml of ethanol and 15 ml of 20% NaOH was added and the mixture was refluxed for 1 h. 4.3 mL octyl p-toluenesulfonate was added in portions with stirring until the color changed to red. The resulting precipitate was filtered, the filtrate was diluted with 100 mL water and extracted with 100 mL chloroform. The organic extraction was dried with anhydrous sodium sulfate and evaporated in vacuo. Column chromatography on silica gel using dichloromethane and hexanes mixed solvents yielded the pure title compound as a white solid (1.24 g, 62%). 1HNMR (CDCl3): δ 0.88-0.91 (6H, t, J=7 Hz), 1.31-1.38 (16H, m), 1.54-1.58 (4H, m), 1.84-1.89 (4H, m), 4.26-4.29 (4H, J=7 Hz), 7.36-7.37 (2H, d, J=6 Hz), 7.47-7.48 (2H, d, J=6 Hz).

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. filtrationThe resulting precipitate was filtered
  3. additionthe filtrate was diluted with 100 mL water
  4. extractionextracted with 100 mL chloroform
  5. extractionThe organic extraction
  6. dry with materialwas dried with anhydrous sodium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-ea032b36439f458aa4e07106644267b7
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08436134B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes