Ethylene Glycol → HCID 68124126, compound

HRID 328514Notes

Reaction equation

HRID 328514 reaction equation
[OH:1][CH:2]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][CH2:4][C@@H:5]1[C@@H:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8](=[O:21])[CH2:7][CH2:6]1.C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:45](O)[CH2:46][OH:47]>O>[CH2:45]1[CH2:46][O:47][CH:7]2[CH:8]([C@@H:9]([C@@H:5]([CH2:4][CH2:3][CH:2]([OH:1])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:6]2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[O:21]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 521998p-Toluenesulfonic acid monohydrateHCID 1859466215-Hydroxy-9-oxoprostanoic acid, ethyl ester

Product 1

HCID 68124126HCID 68124126, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3.4 g. of ethyl 15-hydroxy-9-oxo-prostanoate (Example 50) in 85 ml. of benzene containing 30 mg. of p-toluensulfonic acid monohydrate and 2 ml. of ethylene glycol is stirred at the reflux temperature for 18 hours. The water formed is removed by means of a Dean-Stark distilling receiver. The cooled solution is washed with 5% aqueous sodium carbonate solution, saturated sodium chloride solution, dried with anhydrous sodium sulfate and evaporated to dryness under reduced pressure to give 3.78 g. (99%) of oil; λ max. 2.93 (hydroxy group) and 5.77 β (ester carbonyl group).

Workup

  1. customis removed by means of a Dean-Stark
  2. distillationdistilling receiver
  3. washThe cooled solution is washed with 5% aqueous sodium carbonate solution, saturated sodium chloride solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customto give 3.78 g

Sources & evidence

ORD record
ord-d1cafbf34e604e54b4eac712c4d1401e
Source dataset
uspto-grants-1977_04
Patent number
US04017534

Reaction notes

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