Ethylene Glycol → Methyl 1,4-dioxaspiro[4.5]decane-8-carboxylate

HRID 2396737Notes

Reaction equation

HRID 2396737 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1.[CH2:12](O)[CH2:13][OH:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[O:14]1[C:2]2([CH2:7][CH2:6][CH:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]2)[O:1][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 226643Methyl 4-oxocyclohexanecarboxylate

Product 1

HCID 10845708Methyl 1,4-dioxaspiro[4.5]decane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 8 g (0.51 mole) of methyl 4-oxocyclohexane-1-carboxylate in 50 ml of dry benzene is added 4 g (0.064 mole) of ethylene glycol and 0.10 g of p-toluenesulfonic acid and this mixture is refluxed overnight with a Dean-Stark apparatus. The cooled reaction is allowed to stand and the bottom layer (ethylene glycol) separated and the remaining benzene layer washed with aqueous sodium bicarbonate, dried over MgSO4, and stripped to dryness, giving methyl 1,4-dioxaspiro[4,5]decane-8-carboxylate as a clear liquid residue. This material is used without further purification in the next step.

Workup

  1. temperaturethis mixture is refluxed overnight with a Dean-Stark apparatus
  2. customThe cooled reaction
  3. customthe bottom layer (ethylene glycol) separated
  4. washthe remaining benzene layer washed with aqueous sodium bicarbonate
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-aec65cb3121f481492d6fe5ac2f9150e
Source dataset
uspto-grants-1996_02
Patent number
US05494918

Reaction notes

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