ChemicalBook CAS DataBase List diisopropyl oxalate

diisopropyl oxalate synthesis

7synthesis methods

Product Name:diisopropyl oxalate
CAS Number:615-81-6
Molecular formula:C8H14O4
Molecular Weight:174.19

144-62-7 Synthesis

144-62-7
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67-63-0 Synthesis

67-63-0
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Yield: 90%

Reaction Conditions:

with toluene-4-sulfonic acid in toluene for 24 h;Reflux;

Steps:

1 Example 1. Synthesis of Diisopropyl Oxalate from Oxalic Acid
Oxalic acid (1 kg, 11.1 mol) was added to isopropyl alcohol (1700 mL) under stirring in a 5 L laboratory reactor. A clear solution formed. Subsequently, p-toluenesulfonic acid monohydrate (47.67 g, 2.5 mol ) in 200 mL toluene was slowly added to the solution. The reaction mixture was heated up and stirred a reflux for 24 h. The generated water was continuously removed by azeotrope with a Dean-Stark trap to drive the reaction to completion. The reaction mixture was cooled down, neutralized with 500 mL satd. aq. N_aHCO₃, and partitioned between with 400 mL (2x) toluene and 1 L (2x) water. The combined organic phases were dried with 1 L of satd. aq. NaCl solution. The organic phase was separated, and the solvent was removed under vacuum. The crude material was purified by distillation under high vacuum with heating to obtain 1740 g (90%) diisopropyl oxalate as colorless oil. ^l3C NMR (100 MHz, CDCl₃) δ (ppm) 157.96, 71,44, 21.63 (Figure 1 A); ¹H NMR (400 MHz, CDCl₃) δ 5.13 (hept, J= 6.3 Hz, 2 H), 1.33 (d, J = 6.2 Hz, 12 H) (Figure 1B).

References:

KEMIN INDUSTRIES, INC. WO2021/102115, 2021, A1 Location in patent:Paragraph 0095-0097