4-Toluenesulfonyl chloride → 2-Thiopheneethanol tosylate

HRID 1704632Notes

Reaction equation

HRID 1704632 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][OH:8].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.C(N(CC)CC)C.C(OC(C)C)(C)C>O>[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15]([O:8][CH2:7][CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 7914Diisopropyl EtherHCID 8471TriethylamineHCID 794002-Thiopheneethanol

Product 1

HCID 36820342-Thiopheneethanol tosylateYield 90.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.32 kg (65 moles) of the 2-(2-thienyl)-ethanol obtained in 1. above are mixed with 12.68 kg (66.6 moles) paratoluene sulfonyl chloride and 6.8 kg (67.2 moles) triethylamine and with 63 liters diisopropyl ether at room temperature. After stirring during 70 hours, the reaction mixture is poured over 40 liters water. The organic phase is washed with carbonated water and then with pure water until neutral, after which it is dried over sodium sulfate. Evaporation of the solvent gives 16.62 g (Yield: 90.60%) 2-(2-thienyl)-ethyl paratoluene sulfonate.

Workup

  1. washThe organic phase is washed with carbonated water
  2. dry with materialwith pure water until neutral, after which it is dried over sodium sulfate
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-92a4b40b0668426c99e30cd888ff6744
Source dataset
uspto-grants-1978_11
Patent number
US04127580

Reaction notes

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