2-Chloroethanol → Methanesulfonic Acid [2-[(3,4-dichlorophenyl)thio]ethyl]ester

HRID 330404Notes

Reaction equation

HRID 330404 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[Cl:8].ClC1C=C(S)C=CC=1Cl.ClCCO.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][CH2:11][O:12][S:34]([CH3:33])(=[O:36])=[O:35])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 5

HCID 342-ChloroethanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 799643,4-DichlorobenzenethiolHCID 27582053,4-Dichlorophenylthioethanol

Product 1

HCID 14050283Methanesulfonic Acid [2-[(3,4-dichlorophenyl)thio]ethyl]esterYield 47.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 2-[(3,4-dichlorophenyl)thio]ethanol (117.97 g, 0.53 mole) prepared from 3,4-dichlorothiophenol and 2-chloroethanol, in benzene (500 ml) with triethylamine (53.5 g, 0.53 mole) was prepared. To this solution was added dropwise a benzene solution of methanesulfonyl chloride (60.9 g, 0.53 mole) over 1 hr (in an ice bath). The reaction mixture was stirred at room temperature overnight and then filtered. Solvent was removed by evaporation to give an oil which crystallized. A 5 g portion was recrystallized from isopropyl ether to give 4.61 g (47.9% yield based on aliquot) of white crystalline solid, m.p. 53°-55° C.

Workup

  1. customwas prepared
  2. filtrationfiltered
  3. customSolvent was removed by evaporation
  4. customto give an oil which
  5. customcrystallized
  6. customA 5 g portion was recrystallized from isopropyl ether
  7. customto give 4.61 g (47.9% yield based on aliquot) of white crystalline solid, m.p. 53°-55° C.

Sources & evidence

ORD record
ord-98ed3a593c8f4eddbf9ed87be677fe92
Source dataset
uspto-grants-1990_01
Patent number
US04895840

Reaction notes

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