Sulfuric Acid → 1,3-DITHIANE-2-CARBONYL CHLORIDE

HRID 268323

Reaction equation

HRID 268323 reaction equation
OS(O)(=O)=O.[S:6]1[CH2:11][CH2:10][CH2:9][S:8][CH:7]1[C:12]([OH:14])=O.C(Cl)(=O)C([Cl:18])=O>C1C=CC=CC=1>[S:6]1[CH2:11][CH2:10][CH2:9][S:8][CH:7]1[C:12]([Cl:18])=[O:14]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 65578Oxalyl chlorideHCID 3037051,3-Dithiane-2-carboxylic acid

Product 1

HCID 122220081,3-DITHIANE-2-CARBONYL CHLORIDE

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a 500 ml. reaction flask equipped with a reflux condenser connected with a wash-bottle containing H2SO4, there are added 250 ml. of anhydrous benzene (distilled upon sodium), 42 g (0.25 mol) of 1.3-dithiane-2-carboxylic acid (as prepared in example 1) and 28 ml. (0.4 mol) of freshly distilled oxalyl chloride. The mixture is stirred at room temperature and at the end of gaseous evolution, the mixture is heated up to 45° C to complete the gas evolution. The solvent and the excess of oxalyl chloride are evaporated under reduced pressure and the residue is crystallized from dried cyclohexane to yield 1.3-dithiane-2-carboxylic acid chloride.

Workup

  1. customreaction flask
  2. customequipped with a reflux condenser
  3. additionare added 250 ml
  4. temperaturethe mixture is heated up to 45° C
  5. customThe solvent and the excess of oxalyl chloride are evaporated under reduced pressure
  6. customthe residue is crystallized from dried cyclohexane

Sources & evidence

ORD record
ord-6495b24d022747268f8f4b0fcc14670a
Source dataset
uspto-grants-1976_03
Patent number
US03947469

Linked notes

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