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ChemicalBook CAS DataBase List Glutaric acid
110-94-1

Glutaric acid synthesis

13synthesis methods
glutaric acid is produced as a by-product of the production process of adipic acid (about 2% of the output of an adipic acid plant is glutaric); Glutaric acid can be produced through various chemical routes, for example, from cyclopentane by oxidation with molecular oxygen and cobalt (III) catalysts or by ozonolysis; and from cyclopentanol–cyclopentanone by oxidation with oxygen and Co(CH3CO2)2, with potassium peroxide in benzene, or with N2O4 or nitric acid. Together with succinic acid, glutaric acid is formed as a by-product during oxidation of cyclohexanol–cyclohexanone in the adipic acid production process.
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Yield:110-94-1 100%

Reaction Conditions:

with dmap;triethylamine in dichloromethane;

Steps:

1.1 (1)

(1) Glutaric Acid, Trimethylsilylethyl Ester A solution of 1.30 g of trimethylsilylethanol (11.0 mmol, 1.1 eq), 1.14 g of glutaric anhydride (10 mmol, 1.0 eq), 1.53 mL of Et3N (11 mmol, 1.1 eq) and 122 mg of DMAP (1 mmol, 0.1 eq) in 50 mL of CH2Cl2 was stirred under N2 for 18 h. The solution was partitioned between CH2Cl2 (250 mL) and 1M HCl (600 mL) and the organic layer was dried and evaporated to give 2.34 g of the glutaric acid monoester (100%). 1H NMR (300 MHz, CDCl3) δ4.18 (m, 2H), 2.41 (t, J=7.2 Hz, 2H), 2.38 (t, J=7.2 Hz, 2H), 1.9 (quintet, J=7.2 Hz, 2H), 0.97 (m, 2H), 0.04 (s, 9H).

References:

US6190920,2001,B1

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