Hydrochloric Acid → 4-Methylthiobenzyl alcohol methanesulfonate

HRID 850250Notes

Reaction equation

HRID 850250 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[CH3:11][S:12](Cl)(=[O:14])=[O:13].C(N(CC)CC)C.Cl>C1(C)C=CC=CC=1>[CH3:11][S:12]([O:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1)(=[O:14])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 592968[4-(Methylsulfanyl)phenyl]methanol

Product 1

HCID 543237644-Methylthiobenzyl alcohol methanesulfonateYield 80.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
10 °C

Procedure

In a sulfonating flask, 50 g (0.32 mol) of 4-methylthiobenzyl alcohol and 46.3 g (0.32 mol) of methylsulfonyl chloride are dissolved in 250 ml of toluene and, with cooling at 10° C., 32.5 g (0.32 mol) of triethylamine are added dropwise. The reaction mixture is then heated to room temperature and stirred overnight. 400 ml of 2N hydrochloric acid are then added to the reaction solution slowly and with cooling. The phases are separated and the organic phase is washed with water, dried over MgSO4 and concentrated in a rotary evaporator. 60 g (80%) of 4-methylthiobenzyl alcohol methanesulfonate are obtained in the form of a yellow oil.

Workup

  1. temperatureThe reaction mixture is then heated to room temperature
  2. temperaturewith cooling
  3. customThe phases are separated
  4. washthe organic phase is washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-ea819aaf204143cc9fc2fdc2d2f8d40d
Source dataset
uspto-grants-2000_01
Patent number
US06017675

Reaction notes

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