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

HRID 1857055Notes

Reaction equation

HRID 1857055 reaction equation
[C:1]1([CH3:11])[CH:6]=CC(S(O)(=O)=O)=CC=1.[Cl:12][CH2:13][C@H:14]([OH:17])[CH2:15][OH:16]>CC(C)=O>[Cl:12][CH2:13][C@H:14]1[CH2:15][O:16][C:1]([CH3:6])([CH3:11])[O:17]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 148793(2R)-3-Chloro-1,2-propanediol

Product 1

HCID 2734443(R)-(+)-4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolaneYield 7,726%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

p-Toluenesulfonic acid (0.86 g) was added to a mixture of (R)-3-chloro-1,2-propanediol (50.13 g, 0.454 mol, optical purity 98.7% e.e.) and acetone (660 ml) and the resulting mixture was stirred for 12 hours at 25C. After completion of the reaction, acetone was removed in vacuo and the crude product was distilled to give 58.11 g of (R)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane (yield 85%, b.p. 63° C. at 25 mmHg).

Workup

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

Sources & evidence

ORD record
ord-e2a1274e947e4a869990a8069b1d689a
Source dataset
uspto-grants-2000_11
Patent number
US06143908

Reaction notes

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