Hydrochloric Acid → Dimethylmalonyl Dichloride

HRID 258971

Reaction equation

HRID 258971 reaction equation
[CH3:1][C:2]([CH3:9])([C:6](O)=[O:7])[C:3](O)=[O:4].S(Cl)([Cl:12])=O.[ClH:14].S(=O)=O>>[CH3:1][C:2]([CH3:9])([C:6]([Cl:12])=[O:7])[C:3]([Cl:14])=[O:4]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 11686Dimethylmalonic acid2×HCID 24386Thionyl Chloride

Product 1

HCID 4523180Dimethylmalonyl Dichloride

Procedure

To a 500 ml. one-necked flask equipped with reflux condenser with drying tube, is added 50 grams (0.38 mole) dimethylmalonic acid (Aldrich Chemical Co.) and 300 ml. thionyl chloride. The mixture is heated to reflux for about 1 hour during which time the dimethylmalonic acid is dissolved and hydrogen chloride and sulfur dioxide are evolved. The unreacted thionyl chloride is removed by distillation under reduced pressure. The residue is recrystallized twice from cyclohexane to yield a white solid, M.P. 186°-187° C.

Workup

  1. customone-necked flask equipped
  2. temperaturewith reflux condenser
  3. customwith drying tube
  4. temperatureThe mixture is heated
  5. dissolutionis dissolved
  6. customThe unreacted thionyl chloride is removed by distillation under reduced pressure
  7. customThe residue is recrystallized twice from cyclohexane
  8. customto yield a white solid, M.P. 186°-187° C.

Sources & evidence

ORD record
ord-38581de9b1114be4935b945dafac826a
Source dataset
uspto-grants-1977_07
Patent number
US04035437

Linked notes

Loading…