Hydrochloric Acid → 2-Acetoxyethyl chloromethyl sulfide

HRID 848092

Reaction equation

HRID 848092 reaction equation
[ClH:1].[C:2]([O:5][CH2:6][CH2:7][SH:8])(=[O:4])[CH3:3].[CH2:9]=O.[Cl-].[Ca+2].[Cl-]>C(Cl)Cl>[Cl:1][CH2:9][S:8][CH2:7][CH2:6][O:5][C:2](=[O:4])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 98505Ethanol, 2-mercapto-, 1-acetateHCID 5284359Calcium Chloride

Product 1

HCID 128996102-Acetoxyethyl chloromethyl sulfide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hydrogen chloride gas was introduced into a mixture of 2-acetoxyethanethiol (24.0 g) and paraformaldehyde (6.0 g) at a moderate rate with external cooling for 3 hours. Calcium chloride (25 g) was added and the reaction mixture allowed to stand in a salt-ice bath for 4 hours. Methylene chloride (200 ml) was added, the reaction mixture filtered and the solvent evaporated with rigorous exclusion of moisture. The residual oil was distilled to give 2-acetyloxyethyl chloromethyl sulfide (18.5 g, bp 82°-87° C. at 3 mm Hg).

Workup

  1. temperaturewith external cooling for 3 hours
  2. filtrationthe reaction mixture filtered
  3. customthe solvent evaporated with rigorous exclusion of moisture
  4. distillationThe residual oil was distilled

Sources & evidence

ORD record
ord-fc2246409df24526af69bcb58888db99
Source dataset
uspto-grants-1981_10
Patent number
US04294831

Linked notes

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