Ethylene Glycol → HCID 14496298, compound

HRID 1416547Notes

Reaction equation

HRID 1416547 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:13](O)[CH2:14][OH:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]1[O:15][CH2:14][CH2:13][O:5]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 729332-Chloro-5-nitrobenzaldehyde

Product 1

HCID 14496298HCID 14496298, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Chloro-5-nitrobenzaldehyde (18.6 g), ethylene glycol (18.6 ml), p-toluenesulfonic acid (monohydrate), (0.1 g), were refluxed in toluene (150 mL) for 3 hours. Water was removed azeotropically with a Dean-Stark trap. The reaction mixture was then transfered to seperatory funnel, washed with aqueous bicarbonate, water, dried (MgSO4), filtered and evaporated producing 22.2 g of 2-(2- chloro-5-nitrophenyl-1,3-dioxolane as a white solid, m.p. 78-81° C.

Workup

  1. customWater was removed azeotropically with a Dean-Stark trap
  2. customThe reaction mixture was then transfered to seperatory funnel
  3. washwashed with aqueous bicarbonate, water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-d0cd842d440d4ca0ade576ef4db60c8a
Source dataset
uspto-grants-1999_06
Patent number
US05914351

Reaction notes

Loading…