Ethylene Glycol → HCID 86737061, compound

HRID 1706857Notes

Reaction equation

HRID 1706857 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[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]21OCCO2)[CH3:2].[CH:30]1[CH:35]=CC=CC=1.[CH2:36]([OH:39])[CH2:37][OH:38].C1(C)C=CC(S(O)(=O)=[O:47])=CC=1>C(OCC)C.O>[CH2:1]([O:3][C:4](=[O:29])[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:24][CH2:30][CH2:35][O:47][C:19]2([O:38][CH2:37][CH2:36][O:39]3)[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:13][CH2:12]1)[CH3:2]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 70595169HCID 70595169, compound

Product 1

HCID 86737061HCID 86737061, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2 g of 9,9-ethylenedioxy-15-oxo-13-prostenoic acid ethyl ester, 100 ml of dry benzene, 10 ml of ethyleneglycol and 0.2 g of p-toluenesulphonic acid is boiled for 20 hours on a water separator. After cooling the mixture is diluted with 100 ml of diethyl ether 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 the mixture
  2. washwashed with aqueous NaHCO3 solution and water
  3. dry with materialThe organic phase is dried over Na2SO4
  4. distillationthe solvent is distilled
  5. customAfter chromatographic purification of the residue (silica gel/diisopropyl ether), 9,9

Sources & evidence

ORD record
ord-4b156dea4f4840f5a2c483c1be86fbb7
Source dataset
uspto-grants-1980_06
Patent number
US04209444

Reaction notes

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