Ethylene Glycol → Methyl 1,4-dioxaspiro[4.4]nonane-6-carboxylate

HRID 31702Notes

Reaction equation

HRID 31702 reaction equation
O.[CH3:2][O:3][C:4]([CH:6]1[C:10](=[O:11])[CH2:9][CH2:8][CH2:7]1)=[O:5].[CH2:12](O)[CH2:13][OH:14].C1C=CC=CC=1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>[CH3:2][O:3][C:4]([CH:6]1[CH2:7][CH2:8][CH2:9][C:10]21[O:14][CH2:13][CH2:12][O:11]2)=[O:5]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 962WaterHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl ester

Product 1

HCID 10559447Methyl 1,4-dioxaspiro[4.4]nonane-6-carboxylateYield 70.3%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8471TriethylamineSolvent

Procedure

A reflux condenser equipped with a Dean-Stark water separator was attached to a round bottom flask containing methyl 2-cyclopentanonecarboxylate (2 ml, 16.2 mmol), ethylene glycol (994 μl, 17.8 mmol), p-toluenesulfonic acid monohydrate (139 mg, 0.73 mmol), and benzene (30 ml). The mixture was heated under reflux for 2 hours. To the reaction mixture, triethylamine (0.22 ml) was added and the mixture was concentrated and purified by silica gel column chromatography (elution solvent: ethyl acetate/heptane=1/9, 1/1) to obtain the title compound (2.12 g, yield 70.3%) as a colorless oil.

Workup

  1. customseparator was attached to a round bottom flask
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. concentrationthe mixture was concentrated
  5. custompurified by silica gel column chromatography (elution solvent: ethyl acetate/heptane=1/9, 1/1)

Sources & evidence

ORD record
ord-a82e1a1507d34912b48aa00517981582
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

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