Ethylene Glycol → HCID 20040403, compound

HRID 4488Notes

Reaction equation

HRID 4488 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH2:15])(=[O:14])=[O:13])[C:2](=[O:4])[CH3:3].[CH2:16](O)[CH2:17][OH:18].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH3:3][C:2]1([CH2:1][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[S:12]([NH2:15])(=[O:14])=[O:13])[O:18][CH2:17][CH2:16][O:4]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 21694700HCID 21694700, compound

Product 1

HCID 20040403HCID 20040403, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4.58 g of 2-(2-propanon-1-yloxy)phenylsulfonamide, 2 ml of ethylene glycol, 0.02 g of p-toluenesulfonic acid and 30 ml of toluene is heated for 7 hours to reflux while simultaneously separating the water of reaction. The cooled solution is taken up in 80 ml of ethyl acetate and the organic phase is washed with saturated sodium bicarbonate solution and water, dried and concentrated, affording 5 g of 2-(2-methyl-1,3-dioxolan-2-yl-methoxy)phenylsulfonamide in the form of a yellow viscous oil which can be further used without purification.

Workup

  1. temperatureis heated for 7 hours
  2. temperatureto reflux
  3. customwhile simultaneously separating
  4. customthe water of reaction
  5. washthe organic phase is washed with saturated sodium bicarbonate solution and water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-983466e81fae4be2b37209716d2579ca
Source dataset
uspto-grants-1988_02
Patent number
US04726836

Reaction notes

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