Ethylene Glycol → Ethyl 1,4-dioxaspiro[4.5]decane-6-carboxylate

HRID 1594156Notes

Reaction equation

HRID 1594156 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH2:13](O)[CH2:14][OH:15].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1.C(OCC)C>[O:15]1[C:2]2([CH2:7][CH2:6][CH2:5][CH2:4][CH:3]2[C:8]([O:10][CH2:11][CH3:12])=[O:9])[O:1][CH2:13][CH2:14]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 95543Ethyl 2-oxocyclohexanecarboxylate

Product 1

HCID 336004Ethyl 1,4-dioxaspiro[4.5]decane-6-carboxylate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

Ethyl 2-oxocyclohexane carboxylate (11.3 g) and ethylene glycol (11 mL) were dissolved in toluene (100 mL). To the reaction mixture camphorsulfonic acid (1.03 g) was added and refluxed for 8 hours with Dean-Stark apparatus. The reaction mixture was cooled to room temperature, diluted with diethyl ether and washed with saturated aqueous sodium hydrogencarbonate solution. The extract washed with saturated brine, dried over anhydrous magnesium sulfate, and from which the solvent was distilled off to provide a crude product of the title compound.

Workup

  1. temperaturerefluxed for 8 hours with Dean-Stark apparatus
  2. washwashed with saturated aqueous sodium hydrogencarbonate solution
  3. washThe extract washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationfrom which the solvent was distilled off

Sources & evidence

ORD record
ord-b88bccb8684644c5be2b1e9b0c3fbe77
Source dataset
uspto-grants-2007_11
Patent number
US07300947B2

Reaction notes

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