Ethylene Glycol → HCID 20504189, compound

HRID 1702135Notes

Reaction equation

HRID 1702135 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[O:8])[CH:2]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:30](O)[CH2:31][OH:32]>C1(C)C(C)=CC=CC=1>[Cl:17][C:11]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=1[CH2:9][C:7]1([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[O:32][CH2:31][CH2:30][O:8]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 136712392,4-Dichlorobenzyl 3-pyridyl ketone

Product 1

HCID 20504189HCID 20504189, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2.25 g of 2,4-dichlorobenzyl 3-pyridyl ketone, 2.2 g of p-toluenesulfonic acid monohydrate and 1.0 g of ethylene glycol are heated at reflux for 24 hours in 20 ml of xylene, the resulting water being separated in a water separator. The mixture is then cooled, poured into 2N sodium hydroxide and extracted with diethyl ether, the organic phase is dried over anhydrous sodium sulfate and the solvent is removed under reduced pressure. The crude product is purified by chromatography on silica gel with n-hexane/ethyl acetate (1:1) to yield 3-[2-(2,4-dichlorobenzyl)-1,3-dioxolan-2-yl]pyridine, which melts at 76°-78°.

Workup

  1. customthe resulting water being separated in a water separator
  2. temperatureThe mixture is then cooled
  3. additionpoured into 2N sodium hydroxide
  4. extractionextracted with diethyl ether
  5. dry with materialthe organic phase is dried over anhydrous sodium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customThe crude product is purified by chromatography on silica gel with n-hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-5cbd657376cf4560bfb2c1a2029f29eb
Source dataset
uspto-grants-1983_04
Patent number
US04380544

Reaction notes

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