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

HRID 1093105Notes

Reaction equation

HRID 1093105 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6]1[CH2:12][CH2:11][C:9](=[O:10])[CH2:8][CH2:7]1)=[O:5].[CH2:13](O)[CH2:14][OH:15].CCOCC>C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:15]1[C:9]2([CH2:11][CH2:12][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH2:8]2)[O:10][CH2:13][CH2:14]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 3283Diethyl EtherHCID 317638Ethyl 4-oxocyclohexanecarboxylate2×

Product 1

HCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 241BenzeneSolvent

Procedure

This compound was prepared from ethyl cyclohexanone-4-carboxylate by following the procedure of Pearson et al. (J. Org. Chem., 1997, 62, 5284). A mixture of ethylene glycol (131 mL, 2350 mmol), ethyl 4-oxocyclohexanecarboxylate (100 g, 588 mmol), and p-toluene sulfonic acid monohydrate (2.012 g, 10.58 mmol) in benzene (125 mL) was stirred overnight at room temperature, under N2. The solution was poured into Et2O (1 L) and the mixture washed with water (3×300 mL), sat. NaHCO3 (100 mL) followed by brine (100 mL). The organic layer was then dried (MgSO4), filtered, and concentrated to yield the title compound (125.5 g, 586 mmol, 100% yield) as a clear oil: LCMS m/z 215.13 (M+H).

Workup

  1. washthe mixture washed with water (3×300 mL), sat. NaHCO3 (100 mL)
  2. dry with materialThe organic layer was then dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-68c89c19d1334a1e89152ceeb3b28fbf
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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