Ethylene Glycol → HCID 20399662, compound

HRID 1981095Notes

Reaction equation

HRID 1981095 reaction equation
Cl[CH:2]([Cl:10])[C:3]([NH:5][CH2:6][C:7](=[O:9])[CH3:8])=[O:4].[CH2:11](O)[CH2:12][OH:13].ClC(Cl)C.C(=O)([O-])[O-].[K+].[K+]>C1C2C(=CC=CC=2)C=CC=1S(O)(=O)=O.O>[CH3:8][C:7]1([CH2:6][NH:5][C:3](=[O:4])[CH2:2][Cl:10])[O:9][CH2:11][CH2:12][O:13]1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 63651,1-DichloroethaneHCID 11430Potassium CarbonateHCID 132331232,2-Dichloro-N-(2-oxopropyl)acetamide

Product 1

HCID 20399662HCID 20399662, compoundYield 34.4%

Reagents, catalysts & solvents 2

HCID 84202-Naphthalenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

Six g of 3-(dichloroacetylamino)-2-propanone (0.03 mole), 2.0 g (0.03 mole) of ethylene glycol, 0.2 g of β-naphthalene sulfonic acid, and 100 ml of dichloroethane were combined in a reaction flask and refluxed until water stopped coming off. Then the reaction was stirred with potassium carbonate and filtered over Florisil. The filtrate was evaporated to yield 2.0 g of 2-methyl-2-(chloroacetylamino)methyl-1,3-dioxolane, a white solid. m.p.=128°-130° C. Structure was confirmed by NMR.

Workup

  1. filtrationfiltered over Florisil
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-064c3cf2fdfd449ea0b6895fbb6f60bd
Source dataset
uspto-grants-1985_04
Patent number
US04512796

Reaction notes

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