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

HRID 1512159Notes

Reaction equation

HRID 1512159 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].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)C>[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 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-oxo-cyclohexanecarboxylic acid ethyl ester (5.0 g, 29.4 mmol), ethylene glycol (5.7 mL, 102 mmol) and p-toluenesulfonic acid (0.067 g, 0.35 mmol) in toluene (15 mL) was stirred at room temperature for 18 h. The resulting solution was diluted with ethyl ether (20 mL). The organic layer was washed successively with water and brine, separated and dried with sodium sulfate, filtered and concentrated to yield 1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester.

Workup

  1. washThe organic layer was washed successively with water and brine
  2. customseparated
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8ff72d58549f4b9692669dc50aa14de7
Source dataset
uspto-grants-2012_07
Patent number
US08217060B2

Reaction notes

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