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

HRID 1093069Notes

Reaction equation

HRID 1093069 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]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)C>[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

5

Reactant 2

HCID 174Ethylene GlycolHCID 317638Ethyl 4-oxocyclohexanecarboxylate

Product 1

HCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylateYield 94%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of ethyl 4-oxocyclohexanecarboxylate (500 g, 2.94 mol), ethane-1,2-diol (656 mL, 11.76 mol) and p-toluene sulfonic acid (10.06 g, 0.053 mol) was stirred at room temperature under nitrogen atmosphere for 3 days. After pouring in to diethyl ether (1 L), the mixture was washed with water (500 ml), dilute NaHCO3 solution (300 mL) followed by brine (500 mL). The organic layer was then dried (Na2SO4) filtered and concentrated to afford (590 g, 94% yield) the title compound as a colorless oil. Ref. J. Org. Chem. 1997, 62, 5284-5292.

Workup

  1. washthe mixture was washed with water (500 ml), dilute NaHCO3 solution (300 mL)
  2. dry with materialThe organic layer was then dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9381e958df3c422287a55679d8d66cc0
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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