3-Chloro-1,2-propanediol → 2,4-bis(chloromethyl)-1,3-dioxolane

HRID 1935984Notes

Reaction equation

HRID 1935984 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][Cl:5].[Cl:8][CH2:9]C(O)CO>CC1C=CC(S(O)(=O)=O)=CC=1>[Cl:5][CH2:4][CH:3]1[O:6][CH:7]([CH2:9][Cl:8])[CH2:1][O:2]1

Participants

4

Reactant 2

HCID 72903-Chloro-1,2-propanediolHCID 609862-Chloro-1,1-dimethoxyethane

Product 1

HCID 2394522,4-bis(chloromethyl)-1,3-dioxolaneYield 93.6%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

124 g (1 mol) of chloroacetaldehyde dimethyl acetal and 110 g (1 mol) of 3-chloro-1,2-propanediol are heated together with 0.3 g p-TSA and the resultant methanol removed by distillation. Once 32 g of methanol have passed over, the reaction mixture is washed with weakly alkaline water, the organic phase separated and dried over Na2SO4. After fractionation, 160 g (93%) of 2,4-bis(chloromethyl)-1,3-dioxolane are obtained. Bp.: 98° C. (1500 Pa); IR: 1191, 1049, 1007 cm−1 (acetal); MS: m/e=169 (M−1), 140, 123, 121, 105, 93, 77, 75, 63, 57.

Workup

  1. customthe resultant methanol removed by distillation
  2. washis washed with weakly alkaline water
  3. customthe organic phase separated
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-54c319539d244620940daf3a2fc5c4d9
Source dataset
uspto-grants-2002_05
Patent number
US06388104B1

Reaction notes

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