Ethylene Glycol → HCID 23333607, compound

HRID 904193Notes

Reaction equation

HRID 904193 reaction equation
[CH3:1][N:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5](=[O:13])[C:4]2[CH:14]=[C:15]([CH2:18][C:19]([OH:21])=[O:20])[CH:16]=[CH:17][C:3]1=2.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:33](O)[CH2:34][OH:35]>>[OH:35][CH2:34][CH2:33][O:20][C:19](=[O:21])[CH2:18][C:15]1[CH:16]=[CH:17][C:3]2[N:2]([CH3:1])[CH2:8][C:7]3[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=3[C:5](=[O:13])[C:4]=2[CH:14]=1

Participants

4

Reactant 3

HCID 174Ethylene Glycol2×HCID 6101p-Toluenesulfonic acidHCID 30524825H-Dibenz(b,e)azepine-2-acetic acid, 6,11-dihydro-5-methyl-11-oxo-

Product 1

HCID 23333607HCID 23333607, compound

Procedure

5,6-Dihydro-5-methyl-11oxodibenz[b,e]azepine-2-acetic acid (2g), ethylene glycol (150 ml), and p-toluene-sulfonic acid (0.05 g) were put into an esterification apparatus, and refluxed for 3 hours. After the reaction, excess ethylene glycol was distilled off under reduced pressure, and the residue was dissolved in chloroform. The solution was washed with a 5% aqueous solution of potassium carbonate, washed in water, and dried over MgSO4. Then, the solvent was distilled off to give 2.1 g of an oily material. The oily material was purified by column chromatography over 50 l g of Wakogel C-200 l and elution of the column with chloroform gave 1.3 g of an oily matter.

Workup

  1. temperaturerefluxed for 3 hours
  2. distillationwas distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washThe solution was washed with a 5% aqueous solution of potassium carbonate
  5. washwashed in water
  6. dry with materialdried over MgSO4
  7. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-9ad74c3daf23475f82accb503094340b
Source dataset
uspto-grants-1980_10
Patent number
US04230703

Reaction notes

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