Ethylene Glycol → HCID 57485780, compound

HRID 2199451Notes

Reaction equation

HRID 2199451 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][C:9](=[O:11])[CH2:8][CH:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:6]1)=[O:4].[CH2:16](O)[CH2:17][OH:18].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:15][O:14][C:12]([CH:7]1[CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:10][C:9]2([O:18][CH2:17][CH2:16][O:11]2)[CH2:8]1)=[O:13]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 13028458Dimethyl 5-oxocyclohexane-1,3-dicarboxylate

Product 1

HCID 57485780HCID 57485780, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-oxocyclohexane-1,3-dicarboxylic acid dimethyl ester (22.8 g, 106.4 mmol), ethylene glycol (13.3 g, 215 mmol) and p-toluenesulfonic acid monohydrate (0.22 g, 1.3 mmol) in toluene (230 mL), in a flask fitted with Dean-Stark trap was heated under reflux for 5 h. The reaction was cooled to room temperature, water was added and the mixture was extracted with ethyl acetate. Organic layer was separated, washed with NaHCO3 solution and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give an oil, which was triturated with hexane and left in the fridge overnight. The precipitated solid was filtered and dried under vacuum to provide 17.1 (63%) g of the title compound, 1,4-Dioxa-spiro[4.5]decane-7,9-dicarboxylic acid dimethyl ester as a white solid. 1HNMR (400 MHz, CDCl3), δ: 3.95 (m, 4H), 3.7 (s, 6H), 2.72-2.62 (m, 3H), 2.32-2.22 (m, 1H), 2.02-1.96 (m, 2H), 1.6-1.4 (m, 3H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 h
  3. extractionthe mixture was extracted with ethyl acetate
  4. customOrganic layer was separated
  5. washwashed with NaHCO3 solution and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto give an oil, which
  9. customwas triturated with hexane
  10. filtrationThe precipitated solid was filtered
  11. customdried under vacuum

Sources & evidence

ORD record
ord-48ac38721d6a4bc28505a04a6c0a01fd
Source dataset
uspto-grants-2016_06
Patent number
US09359297B2

Reaction notes

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