Ethylene Glycol → HCID 86734011, compound

HRID 839334Notes

Reaction equation

HRID 839334 reaction equation
[C:1]([CH2:6][CH:7]1[CH:11]([CH:12]=[CH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:10][CH2:9][C:8]1=O)([O:3][CH2:4][CH3:5])=[O:2].[CH2:21]([OH:24])[CH2:22]O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[C:1]([CH2:6][CH:7]1[O:24][CH:21]2[CH2:22][CH2:8][CH2:9][CH:10]2[CH:11]1/[CH:12]=[CH:13]/[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 521998p-Toluenesulfonic acid monohydrateHCID 70614904HCID 70614904, compound

Product 1

HCID 86734011HCID 86734011, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10.142 g. (0.0362 mole) of 2-(carbethoxymethyl)-3-(1-octenyl)cyclopentanone (ethyl 9-oxo-3,4,5,6,7-pentanor-13-trans-prostenoate, Example 213), 3.49 g. (0.0562 mole) of ethylene glycol, 0.344 g. of p-toluensulfonic acid monohydrate, and 30 ml. of benzene is refluxed for 4.5 hours with azeotropic removal of water. The mixture is cooled, placed onto a column of 130 g. of Florisil® in benzene and the ketal is eluted off with benzene. The filtrate is evaporated to yield 9.53 g. of a colorless oil.

Workup

  1. additionA mixture of 10.142 g
  2. temperatureThe mixture is cooled
  3. washof Florisil® in benzene and the ketal is eluted off with benzene
  4. customThe filtrate is evaporated
  5. customto yield 9.53 g

Sources & evidence

ORD record
ord-ad62817ad31147ef9385737dc561a4ad
Source dataset
uspto-grants-1978_06
Patent number
US04094896

Reaction notes

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