Ethylene Glycol → HCID 86737061, compound

HRID 1706858Notes

Reaction equation

HRID 1706858 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:12]1=O)[CH3:2].[CH:27]1[CH:32]=CC=CC=1.[CH2:33]([OH:36])[CH2:34][OH:35].O.C1(C)C=CC(S(O)(=O)=[O:45])=CC=1>O>[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]23[O:36][CH2:33][CH2:34][O:35][C:19]2([O:45][CH2:32][CH2:27][O:24]3)[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:13][CH2:12]1)[CH3:2]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 521998p-Toluenesulfonic acid monohydrateHCID 57128358HCID 57128358, compound

Product 1

HCID 86737061HCID 86737061, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 500 mg of 9,15-dioxo-13-prostenoic acid ethyl ester, 15 ml of dry benzene, 1 ml of ethyleneglycol and 5 mg of p-toluenesulphonic acid monohydrate is boiled for 16 hours on a water separator. After cooling, the mixture is diluted with 100 ml of diethyl and washed with aqueous NaHCO3 solution and water. The organic phase is dried over Na2SO4 and the solvent is distilled. After chromatographic purification of the residue (silica gel/diisopropyl ether), 9,9;15,15-bis-(ethylenedioxy)-13-prostenoic acid ethyl ester is obtained.

Workup

  1. temperatureAfter cooling
  2. additionthe mixture is diluted with 100 ml of diethyl
  3. washwashed with aqueous NaHCO3 solution and water
  4. dry with materialThe organic phase is dried over Na2SO4
  5. distillationthe solvent is distilled
  6. customAfter chromatographic purification of the residue (silica gel/diisopropyl ether), 9,9

Sources & evidence

ORD record
ord-06cf66b1a9e9486b993962af239aa0d5
Source dataset
uspto-grants-1980_06
Patent number
US04209444

Reaction notes

Loading…