Ethylene Glycol → Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylate

HRID 337489Notes

Reaction equation

HRID 337489 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH2:13](O)[CH2:14][OH:15].C(O)(=O)C(O)=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[O:15]1[C:2]2([CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]2)[O:1][CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 971Oxalic AcidHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 4-oxocyclohexanecarboxylate (5.00 g, 29.4 mmol) was dissolved in toluene (200 mL), and ethylene glycol (15 mL) and oxalic acid (500 mg) were added thereto, followed by stirring under heating and reflux for 5 hours. The reaction mixture was poured into a saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=8:2) to afford ethyl 1,4-dioxaspiro[4,5]decane-8-carboxylate (6.28 g, 99%).

Workup

  1. temperatureunder heating
  2. temperaturereflux for 5 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away under reduced pressure
  7. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=8:2)

Sources & evidence

ORD record
ord-6312ce417e0749bbbea15ccf9ec0ba72
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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