Ethylene Glycol → HCID 13365013, compound

HRID 1154561Notes

Reaction equation

HRID 1154561 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]([N+:13]([O-:15])=[O:14])[C:4]=1[CH:5]=[O:6].[CH2:16](O)[CH2:17][OH:18].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH2:17]1[O:18][CH:5]([C:4]2[C:7]([N+:13]([O-:15])=[O:14])=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[C:3]=2[O:2][CH3:1])[O:6][CH2:16]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 71721272,3-Dimethoxy-6-nitrobenzaldehyde

Product 1

HCID 13365013HCID 13365013, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2,3-dimethoxy-6-nitrobenzaldehyde (16.0 g, 75 mM), ethylene glycol (64 g, 103 mM), and p-toluenesulfonic acid monohydrate (0.2 g) in benzene (750 ml) is refluxed in a Dean-Stark apparatus for 48 hours. The solution is then poured into water (1 l.). The organic phase is washed with saturated aqueous NaHCO3 (2×20 ml), dried over Na2SO4, filtered, and the solvent removed in vacuo. The crude product is recrystallized from n-hexane (2 l.); yield 15.2 g (78.2%); m.p. 74°-76° C.

Workup

  1. temperatureis refluxed in a Dean-Stark apparatus for 48 hours
  2. washThe organic phase is washed with saturated aqueous NaHCO3 (2×20 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe crude product is recrystallized from n-hexane (2 l.)

Sources & evidence

ORD record
ord-f201b2cc4181406ca00b531ba5718ea3
Source dataset
uspto-grants-1984_12
Patent number
US04490374

Reaction notes

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