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

HRID 2089167Notes

Reaction equation

HRID 2089167 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:13](O)[CH2:14][OH:15].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 317638Ethyl 4-oxocyclohexanecarboxylate

Product 1

HCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Oxo-cyclohexanecarboxylic acid ethyl ester (Aldrich, 6.1 g, 35.8 mmol), ethylene glycol (3.34 g, 53.8 mmol), pTSA (123 mg, 0.717 mmol) in toluene (100 mL) was refluxed in Dean-Stark until no water was observed. The resulting solution was washed with saturated NaHCO3 and brine, dried over anhydrous Na2SO4, filtered and concentrated to give 1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester as colorless solid.

Workup

  1. washThe resulting solution was washed with saturated NaHCO3 and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-936bb385892f4f9c8ff6f86fb2c6daa2
Source dataset
uspto-grants-2013_05
Patent number
US08436023B2

Reaction notes

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