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

HRID 2045115Notes

Reaction equation

HRID 2045115 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH2:13](O)[CH2:14][OH:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O>[O:15]1[C:2]2([CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]2)[O:1][CH2:13][CH2:14]1

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-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of ethyl 4-oxocyclohexanecarboxylate (31.8 g) in toluene (100 mL) was added ethylene glycol (36.5 mL) and p-toluenesulfonic acid monohydrate (0.426 g). The two phase mixture was stirred rapidly at ambient temperature for 72 hours. The reaction was diluted with water (900 mL) and extracted with ether (900 mL). The organic layer was washed with saturated sodium bicarbonate solution and brine, and then dried over anhydrous sodium sulfate. After filtration, the title compound was obtained by concentration of the filtrate under high vacuum.

Workup

  1. extractionextracted with ether (900 mL)
  2. washThe organic layer was washed with saturated sodium bicarbonate solution and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration

Sources & evidence

ORD record
ord-21cad1aa321046e4980a7cf2a4d869f4
Source dataset
uspto-grants-2013_11
Patent number
US08586754B2

Reaction notes

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