(2,2-Dimethyl-1,3-dithiolan-4-yl)methanol → 1,3-Dithiolane, 4-(chloromethyl)-2,2-dimethyl-

HRID 256284Notes

Reaction equation

HRID 256284 reaction equation
[CH3:1][C:2]1([CH3:9])[S:6][CH:5]([CH2:7]O)[CH2:4][S:3]1.S(Cl)([Cl:12])=O>C1(C)C=CC=CC=1>[Cl:12][CH2:7][CH:5]1[CH2:4][S:3][C:2]([CH3:9])([CH3:1])[S:6]1

Participants

4

Reactant 2

HCID 21893(2,2-Dimethyl-1,3-dithiolan-4-yl)methanolHCID 24386Thionyl Chloride

Product 1

HCID 223311,3-Dithiolane, 4-(chloromethyl)-2,2-dimethyl-Yield 49.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3.46 g (0.021 mole) of 2,2-dimethyl-4-hydroxymethyl-1,3-dithiolan in 15 mL of toluene was added dropwise 2.35 g (0.020 mole) of thionyl chloride, and the mixture was heated gradually to 80°-85° C., maintained at that temperature for 0.75 hour, then stirred at room temperature for 16 hours. The mixture was filtered, and the filtrate concentrated to dryness at 60° C./100 mm Hg to give a residual oil. Distillation of the oil gave 1.81 g of product, bp 75°-78° C./1.25-1.35 mm Hg.

Workup

  1. temperaturethe mixture was heated gradually to 80°-85° C.
  2. temperaturemaintained at that temperature for 0.75 hour
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated to dryness at 60° C./100 mm Hg
  5. customto give a residual oil
  6. distillationDistillation of the oil

Sources & evidence

ORD record
ord-0669c09553f140b38c9ed133c4840ed6
Source dataset
uspto-grants-1987_10
Patent number
US04702763

Reaction notes

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