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

HRID 854832Notes

Reaction equation

HRID 854832 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6]1[CH2:12][CH2:11][C:9](=[O:10])[CH2:8][CH2:7]1)=[O:5].[CH2:13](O)[CH2:14][OH:15]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:2]([O:3][C:4]([CH:6]1[CH2:12][CH2:11][C:9]2([O:15][CH2:14][CH2:13][O:10]2)[CH2:8][CH2:7]1)=[O:5])[CH3:1]

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 317638Ethyl 4-oxocyclohexanecarboxylate

Product 1

HCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylateYield 99.3%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 4-cyclohexanonecarboxylic acid ethyl ester (5.00 g, 29.38 mmol) and ethylene glycol (2.13 mL, 38.19 mmol) in toluene (150 mL) was heated in a Dean-Stark trap at reflux for 1 h and was then treated with p-toluenesulfonic acid monohydrate (56.74 mg, 0.294 mmol). The reaction solution was heated an additional 30 min at reflux, cooled to 25° C., and concentrated in vacuo. The resulting oil was dissolved in ethyl acetate (200 mL), washed with water (2×50 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford pure 1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (6.25 g, 99.3%) as a colorless oil.

Workup

  1. temperatureat reflux for 1 h
  2. temperatureThe reaction solution was heated an additional 30 min
  3. temperatureat reflux
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resulting oil was dissolved in ethyl acetate (200 mL)
  6. washwashed with water (2×50 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90ed99fc84144c5eb6ddaad0273da223
Source dataset
uspto-grants-2007_08
Patent number
US07259166B2

Reaction notes

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