ChemicalBook CAS DataBase List Hexahydrophthalic anhydride

Hexahydrophthalic anhydride synthesis

10synthesis methods

Product Name:Hexahydrophthalic anhydride
CAS Number:85-42-7
Molecular formula:C8H10O3
Molecular Weight:154.16

Hexahydrophthalic anhydride is obtained by reacting ciscyclohexane-1, 2-dicarboxylic acid with oxalyl chloride.Combine ciscyclohexane-1, 2-dicarboxylic acid (1 mmol, 172 mg) and oxalyl chloride (1.2 mmol, 152 mg, 0.103 ml) in dry toluene (5 mL) and add a drop of freshly distilled DMF. Purge the reaction vessel with argon and heat the reaction under stirring for 3 h. Stop the stirring, decant the toluene solution and filter. Evaporate the volatiles. Transform into crystalline form by trituration with diethyl ether. 1H NMR (400 MHz, CDCl3) δ 3.18 - 3.12 (m, 2H 2CH) 1.96 - 1.83 (m, 4H 2CH2) 1.57 - 1.49 (m, 4H 2CH2). HRMS (ESI), calcd for C8H10NaO3 [M+Na]+ 175.0522, found 175.0527; calcd for C9H14NaO4 [M+CH3 OH+Na]+ 209.0784, found 209.0788.

Fig The synthetic method of Hexahydrophthalic anhydride.

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Yield:-

Steps:

Multi-step reaction with 2 steps
1: 220 - 230 °C / im Vakuum
2: sodium amalgam / Erhitzen des entstehenden Gemisches der stereoisomeren Hexahydrophthalsaeuren im Vakuum auf 210-220grad

References:

Abati;Vergari [Gazzetta Chimica Italiana,1909,vol. 39 II,p. 153]

85-44-9 Synthesis