Ethylene Glycol → Ethyl 9-oxodecanoate ethylene ketal

HRID 27306Notes

Reaction equation

HRID 27306 reaction equation
[O:1]=[C:2]([CH3:15])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=O.[CH2:16]([OH:19])[CH2:17][OH:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:16]1[O:19][C:10]([O:12][CH2:13][CH3:14])([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2](=[O:1])[CH3:15])[O:18][CH2:17]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 12512254HCID 12512254, compound

Product 1

HCID 86737195Ethyl 9-oxodecanoate ethylene ketalYield 83.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution containing 77.5 g (362 mmol) of ethyl 9-oxodecanoate (prepared described in J. Amer. Chem. Soc., 68: 832 [1946]), 22.4 g (362 mmol) of ethylene glycol and 438 mg of p-toluenesulfonic acid in 150 ml of dry benzene was refluxed for 4.5 hr with a Dean Stark trap. A 7.0 ml portion of water (theoretical=6.5 g) collected in the trap. The solution was cooled to room temperature and then was washed with saturated aqueous sodium bicarbonate. The aqueous phase was back-extracted twice with ether. The combined ether extracts were dried over Na2SO4 and evaporated in vacuo and distilled in vacuo to give a 83.5% yield of the title compound. The product had the following physical characteristics:

Workup

  1. temperaturewas refluxed for 4.5 hr with a Dean Stark trap
  2. customA 7.0 ml portion of water (theoretical=6.5 g) collected in the trap
  3. washwas washed with saturated aqueous sodium bicarbonate
  4. extractionThe aqueous phase was back-extracted twice with ether
  5. dry with materialThe combined ether extracts were dried over Na2SO4
  6. customevaporated in vacuo
  7. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-d99ce41a3c704fb3a5b2ad68e7f6be7f
Source dataset
uspto-grants-1980_09
Patent number
US04220795

Reaction notes

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