Water → HCID 13154997, compound

HRID 1935981Notes

Reaction equation

HRID 1935981 reaction equation
[Cl:1][CH2:2][C:3](=[O:5])[CH3:4].[Cl:6][CH2:7][CH:8]([OH:11])[CH2:9]O.O>CC1C=CC(S(O)(=O)=O)=CC=1.C1CCCCC1>[Cl:1][CH2:2][C:3]1([CH3:4])[O:11][CH:8]([CH2:7][Cl:6])[CH2:9][O:5]1

Participants

6

Reactant 3

HCID 962WaterHCID 6571ChloroacetoneHCID 72903-Chloro-1,2-propanediol

Product 1

HCID 13154997HCID 13154997, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8078CyclohexaneSolvent

Procedure

In a similar manner to the preceding Examples, 92.5 g (1 mol) of chloroacetone and 110.5 g (1 mol) of 3-chloro-1,2-propanediol are boiled together in a water separator with 0.5 g of p-TSA and 150 ml of cyclohexane. Once the equivalent quantity of water has separated, the cyclohexane is removed and the residue fractionated. 162 g (87%) of 2,4-bis(chloromethyl)-2-methyl-1,3-dioxolane are obtained. Bp.: 98° C. to 102° C. (1500 Pa); IR: acetal bands at 1120 cm−1, 1098 cm−1, 1053 cm−1, MS: m/e=169 (M−15), 135, 106, 93, 75, 57, 49, 43.

Workup

  1. customOnce the equivalent quantity of water has separated
  2. customthe cyclohexane is removed

Sources & evidence

ORD record
ord-f4453b2d6f5448ef803e7041640b175d
Source dataset
uspto-grants-2002_05
Patent number
US06388104B1

Reaction notes

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