Hydrochloric Acid → [1~1~,2~1~:2~4~,3~1~-Terphenyl]-1~4~,3~4~-dithiol

HRID 1827300Notes

Reaction equation

HRID 1827300 reaction equation
Cl[S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([S:23](Cl)(=O)=O)=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=O)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[SH:2][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([SH:23])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 22137207HCID 22137207, compound

Product 1

HCID 22137213[1~1~,2~1~:2~4~,3~1~-Terphenyl]-1~4~,3~4~-dithiolYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,4″-dichlorosulfonyl1,1′:4′,1″-terphenyl (8.576 g, 20 mmol) synthesized in process 1-a is dissolved in tetrahydrofuran (THF) solvent (300 ml), add lithium aluminium hydride (8.586 g, 200 mmol, 10 eq.) and refluxed for 3 hours. The obtained reacted mixture is poured into ice water, and adjusted the pH to 1 or less by adding concentrated hydrochloric acid. Deposited impurity is removed by suction filtration, then washed by methylene chloride completely. After that, the filtrate is extracted by acid-base extraction (CH2Cl2, NaOH, HCl), the organic phase is dried up using magnesium sulfate and recrystalyzed. Thus, light yellowish crystal of 4,4″-dimercapto-1,1′:4′,1″-terphenyl (3.003 g, 10.2 mmol, 51%) is obtained (compound G).

Workup

  1. temperaturerefluxed for 3 hours
  2. customThe obtained reacted mixture
  3. customDeposited impurity is removed by suction filtration
  4. washwashed by methylene chloride completely
  5. extractionAfter that, the filtrate is extracted by acid-base extraction (CH2Cl2, NaOH, HCl)
  6. customthe organic phase is dried up

Sources & evidence

ORD record
ord-9748678ced5c48a999e3cb8021a26326
Source dataset
uspto-grants-2006_05
Patent number
US07053173B2

Reaction notes

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