p-Toluenesulfonic acid → 4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolane

HRID 1857050Notes

Reaction equation

HRID 1857050 reaction equation
[C:1]1([CH3:11])[CH:6]=CC(S(O)(=O)=O)=CC=1.[Cl:12][CH2:13][CH:14]([OH:17])[CH2:15][OH:16]>CC(C)=O>[Cl:12][CH2:13][CH:14]1[CH2:15][O:16][C:1]([CH3:6])([CH3:11])[O:17]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 72903-Chloro-1,2-propanediol

Product 1

HCID 203744-(Chloromethyl)-2,2-dimethyl-1,3-dioxolaneYield 8,177%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
25 °C

Procedure

p-Toluenesulfonic acid (1.79 g) was added to a mixture of 3-chloro-1,2-propanediol (104.49 g, 0.945 mol) and acetone (1500 ml) and the resulting mixture was stirred for 12 hours at 25° C. After completion of the reaction, acetone was removed in vacuo and the crude product was distilled to give 128.01 g of 4-chloromethyl-2,2-dimethyl-1,3-dioxolane (yield 89%, b.p. 45° C. at 5 mmHg).

Workup

  1. customwas removed in vacuo
  2. distillationthe crude product was distilled

Sources & evidence

ORD record
ord-17f7af8f054d4c2b8e159950eeb481c1
Source dataset
uspto-grants-2000_11
Patent number
US06143908

Reaction notes

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