1,3-Propanedithiol → HCID 11817100, compound

HRID 270212Notes

Reaction equation

HRID 270212 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH2:10]([SH:14])[CH2:11][CH2:12][SH:13]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]2[S:14][CH2:10][CH2:11][CH2:12][S:13]2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 80131,3-PropanedithiolHCID 114773-Chlorobenzaldehyde

Product 1

HCID 11817100HCID 11817100, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 3-chlorobenzaldehyde (100 mmol) in chloroform (250 mL) is added 1,3-propanedithiol (110 mmol). The mixture is chilled to −10° C. and HCl gas is gently bubbled through the mixture for 20 min. The mixture is stirred at −10° C. for one hour, then allowed to warm to room temperature overnight. The solution is washed with 1 M KOH, water, brine, and dried (K2CO3). After filtering, the organic extract is concentrated in vacuo to afford 2-(3-chlorophenyl)-1,3-dithiane.

Workup

  1. customHCl gas is gently bubbled through the mixture for 20 min
  2. temperatureto warm to room temperature overnight
  3. washThe solution is washed with 1 M KOH, water, brine
  4. dry with materialdried (K2CO3)
  5. filtrationAfter filtering
  6. extractionthe organic extract
  7. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-e46b59093c2f4d6bafe52ecfb914df0c
Source dataset
uspto-grants-2008_11
Patent number
US07449490B2

Reaction notes

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