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

HRID 1770118Notes

Reaction equation

HRID 1770118 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-02882bd1f8074dc698cb04586b0b5eb5
Source dataset
uspto-grants-1995_01
Patent number
US05385912

Reaction notes

Loading…