2-Methylbenzenesulfonic acid → 2-Chloromethyl-4,4,6,6-tetramethyl-1,3-dithiane

HRID 127141

Reaction equation

HRID 127141 reaction equation
[Cl:1][CH2:2][CH:3](OC)OC.[CH3:8][C:9]([SH:16])([CH2:11][C:12]([CH3:15])([SH:14])[CH3:13])[CH3:10].C1(C)C(S(O)(=O)=O)=CC=CC=1>>[Cl:1][CH2:2][CH:3]1[S:16][C:9]([CH3:10])([CH3:8])[CH2:11][C:12]([CH3:15])([CH3:13])[S:14]1

Participants

4

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 609862-Chloro-1,1-dimethoxyethaneHCID 202861032,4-Dimethyl-2,4-pentanedithiol

Product 1

HCID 202861232-Chloromethyl-4,4,6,6-tetramethyl-1,3-dithiane

Procedure

2-Chloro-1,1-dimethoxyethane (0.1 mole) and 2,4-dimethyl-2,4-pentanedithiol (0.1 mole) are charged into a glass reaction vessel fitted with a mechanical stirrer, thermometer, Dean Stark trap and reflux condenser. Toluene sulfonic acid (0.1 grams) is added and the reaction mixture is heated and thiol removed. When the thiol evolution ceases, the reaction mixture is then cooled to room temperature, treated with sodium carbonate (5 grams) and filtered. Volatiles are stripped from the filtrate using a rotary evaporator to yield the desired product 2-chloromethyl-4,4,6,6-tetramethyl-1,3-dithiane as the residue.

Workup

  1. customfitted with a mechanical stirrer
  2. temperaturethermometer, Dean Stark trap and reflux condenser
  3. temperaturethe reaction mixture is heated
  4. customthiol removed
  5. additiontreated with sodium carbonate (5 grams)
  6. filtrationfiltered
  7. customa rotary evaporator

Sources & evidence

ORD record
ord-1cebef1484be4b479df47b97bc4f2cf4
Source dataset
uspto-grants-1981_03
Patent number
US04255182

Linked notes

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