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

HRID 1748503Notes

Reaction equation

HRID 1748503 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:17][CH2:18][O:19][C:20]([CH:22]1[CH2:28][CH2:27][C:25](=O)[CH2:24][CH2:23]1)=[O:21]>C1(C)C=CC=CC=1.C(OCC)C>[CH2:18]([O:19][C:20]([CH:22]1[CH2:28][CH2:27][C:25]2([O:4][CH2:1][CH2:2][O:3]2)[CH2:24][CH2:23]1)=[O:21])[CH3:17]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylateYield 73.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

Ethylene glycol (18.2 g) and p-toluenesulfonic acid monohydrate (2.37 g) were added to a solution of 4-cyclohexanonecarboxylic acid ethyl ester (25 g) in toluene (500 ml) and stirred under reflux for 10 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with diethyl ether and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 1,4-dioxaspiro[4,5]decane-8-carboxylic acid ethyl ester (23 g) as a colorless oil.

Workup

  1. temperatureunder reflux for 10 hours
  2. customAfter completion of the reaction
  3. washwashed with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-34d6322aba6b44ddbfd8807799311aa0
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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