Ethylene Glycol → 1-Chloro-3-(1,3-dioxolan-2-yl)-3-methylbutan-2-one

HRID 1253132Notes

Reaction equation

HRID 1253132 reaction equation
[CH3:1][C:2]([CH3:9])([C:5](=[O:8])[CH2:6][Cl:7])[CH:3]=[O:4].[CH2:10](O)[CH2:11][OH:12].O>C(Cl)Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:7][CH2:6][C:5](=[O:8])[C:2]([CH:3]1[O:12][CH2:11][CH2:10][O:4]1)([CH3:9])[CH3:1]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 132699644-Chloro-2,2-dimethyl-3-oxobutanal

Product 1

HCID 132699801-Chloro-3-(1,3-dioxolan-2-yl)-3-methylbutan-2-oneYield 79.8%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

204 g (1.38 mol) of 2,2-dimethyl-4-chloro-3-keto-butanal are heated with 93 g (1.5 mols) of ethylene glycol and 0.7 g of p-toluenesulphonic acid in 400 ml of methylene chloride for 3 hours in a water separator. The organic phase is extracted with 150 ml of 5% strength sodium hydroxide solution, and thereafter with 400 ml of water. The solvent is distilled off and the residue is distilled under the vacuum from a water jet. 211 g (79.8% of theory) of 1-chloro-3-(dioxolan-2-yl)-3-methylbutan-2-one of boiling point 127°-28° C./14 mbar are obtained. ##STR24##

Workup

  1. extractionThe organic phase is extracted with 150 ml of 5% strength sodium hydroxide solution
  2. distillationThe solvent is distilled off
  3. distillationthe residue is distilled under the vacuum from a water jet

Sources & evidence

ORD record
ord-d6f8baa5fb0847a59a869ca163603ef8
Source dataset
uspto-grants-1988_05
Patent number
US04747869

Reaction notes

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