Ethylene Glycol → HCID 57317969, compound

HRID 1763917Notes

Reaction equation

HRID 1763917 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]1[C@@H:15]([CH:16]=[CH:17][C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:13][C@H:12]1[OH:25])[CH3:2].[CH2:27](O)[CH2:28][OH:29].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]1[C:15](=[CH:16][CH2:17][C:18]2([O:29][CH2:28][CH2:27][O:24]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:13][C@H:12]1[OH:25])[CH3:2]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 70616058HCID 70616058, compound

Product 1

HCID 57317969HCID 57317969, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5 g 9β-hydroxy-15-oxo-13-prostenoic acid ethyl ester are boiled with 5 ml ethylene glycol and 0,5 g p-toluene sulfonic acid in 150 ml dry benzene for 20 hours and water is removed. After cooling to room temperature the reaction mixture is given to a mixture of 150 ml saturated aqueous NaHCO3 -solution and 750 ml diethyl ether. The organic layer is separated, washed with water, dried over Na2SO4 and the solvent is removed by destillation. One obtains 15,15-ethylenedioxy-9β-hydroxy-12-prostenoic acid ethyl ester after chromatographical purification of the residue (silicagel/diisopropyl ether); IR: 3500, 1740 and 1470 cm-1.

Workup

  1. customwater is removed
  2. additionis given to a mixture of 150 ml saturated aqueous NaHCO3 -solution and 750 ml diethyl ether
  3. customThe organic layer is separated
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent is removed by destillation

Sources & evidence

ORD record
ord-aae4853a909840639626c61a443ff311
Source dataset
uspto-grants-1978_09
Patent number
US04113863

Reaction notes

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