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

HRID 1960024Notes

Reaction equation

HRID 1960024 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].[C:13]1([CH3:23])C=CC(S(O)(=O)=O)=CC=1.O.C([O-])(O)=[O:26].[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9]2([O:26][CH2:13][CH2:23][O:12]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 516892Sodium Bicarbonate

Product 1

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

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-ethoxycarbonyl cyclohexanone (175 g, 1.03 mol), ethylenegrycol (70 mL), and p-toluenesulfonic acid (2.1 g) in toluene (700 mL) is stirred and refluxed for 6 hours with continuous water removal using Dean-Stark apparatus. After cooling to room temperature, sat. NaHCO3 aq. (1500 mL) and EtOAc (800 mL) are added to the reaction mixture. The organic layer is washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure to afford crude 1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (220 g) as yellow oil, which is used without further purification.

Workup

  1. washThe organic layer is washed with brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-50bffc014242401b90ddd70e8ee8d0c6
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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