Ethylene Glycol → HCID 86745411, compound

HRID 1090728Notes

Reaction equation

HRID 1090728 reaction equation
[O:1]=[C:2]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=O.[CH2:24]([OH:27])[CH2:25][OH:26]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:24]1[O:27][C:5]([O:7][CH2:8][CH3:9])([CH2:4][CH2:3][C:2](=[O:1])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[O:26][CH2:25]1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 15023252HCID 15023252, compound

Product 1

HCID 86745411HCID 86745411, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 9.25 g (28 mmol) of ethyl γ-ketooctadecanoate and 9.00 g of ethylene glycol (145 mmol) was refluxed for 5 hours in 300 ml of toluene in the presence of a small amount of p-toluenesulfonic acid catalyst while removing water by means of Dean-Stark apparatus. The resulting mixture was washed with an aqueous saturated sodium bicarbonate solution and then with an aqueous saturated solution of sodium chloride. An oily product obtained by removing the solvent under reduced pressure was subjected to column chromatography over silica gel (eluent: ethyl acetate/hexane=1/10) to give 7.42 g (71% yield) of ethyl γ-ketooctadecanoate ethylene ketal.

Workup

  1. customwhile removing water by means of Dean-Stark apparatus
  2. washThe resulting mixture was washed with an aqueous saturated sodium bicarbonate solution
  3. customAn oily product obtained
  4. customby removing the solvent under reduced pressure

Sources & evidence

ORD record
ord-83eed6c11e2a46f4baed3f8bbcb43945
Source dataset
uspto-grants-1992_01
Patent number
US05082856

Reaction notes

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