Ethylene Glycol → Methyl 1,4-dioxaspiro[4.5]decane-7-carboxylate

HRID 1684267

Reaction equation

HRID 1684267 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]1.[CH2:12](O)[CH2:13][OH:14].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C1(C)C=CC=CC=1.O>[CH2:12]1[CH2:13][O:14][C:2]2([CH2:7][CH2:6][CH2:5][CH:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]2)[O:1]1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 566099Methyl 3-oxocyclohexane-1-carboxylate

Product 1

HCID 372311Methyl 1,4-dioxaspiro[4.5]decane-7-carboxylate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 22272177Toluene waterSolvent

Conditions

Temperature
95 °C

Procedure

A solution composed of 30 g (192 mmol) of crude methyl 3-oxocyclohexanecarboxylate and 430 cm3 of toluene is introduced into a one-liter three-necked flask equipped with a Dean and Stark apparatus, and 14.3 g (230 mmol) of ethylene glycol are then added with 814 mg (4.3 mmol) of para-toluenesulfonic acid monohydrate. The mixture is heated to reflux, the toluene-water azeotrope forms instantaneously and, after 40 min, no further refluxing of azeotrope (95° C.) takes place. The mixture is maintained for 6 h under reflux of the toluene (110° C.). After cooling, sodium hydrogen carbonate solution is added and the solution is then washed with saturated sodium chloride solution and dried over sodium sulfate. After concentration, 39 g of a yellow oil are obtained, which product is either distilled or chromatographed on a column of 215 g of silica (eluant: cyclo-hexane/ether, 98:2).

Workup

  1. additionis introduced into a one-liter three-necked flask
  2. temperatureThe mixture is heated
  3. temperatureto reflux
  4. temperatureThe mixture is maintained for 6 h
  5. temperatureAfter cooling
  6. washthe solution is then washed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationAfter concentration, 39 g of a yellow oil
  9. customare obtained
  10. distillationeither distilled
  11. customchromatographed on a column of 215 g of silica (eluant: cyclo-hexane/ether, 98:2)

Sources & evidence

ORD record
ord-33d9c668b6f747bc98779db9235d35f4
Source dataset
uspto-grants-1997_06
Patent number
US05639902

Linked notes

Loading…