149302-73-8

Upstream product

• 57-55-6 propylene glycol 
• 79-37-8 oxalyl dichloride 
• 4755-77-5 Ethyl oxalyl chloride 

Downstream Products

• 123-38-6 propionaldehyde 
• 67-64-1 acetone 

Relevant academic research and scientific papers

Cyclocondensation of oxalyl chloride with 1,2-glycols

Oxalyl chloride reacts with a wide range of acyclic 1,2-glycols 1 in the presence of triethylamine to produce 1,3-dioxolan-2-ones 3 together with 1,4-dioxane-2,3-diones 2. Ethylene glycol (1d), monosubstituted ethylene glycols 1e, j-l, and erythro-1,2-disubstituted ethylene glycols 1f, m, o provide the cyclic carbonates 3 as the minor products, while the threo-compounds 1g, i, n, p, q and pinacol (1h) afford 3 as the main products. The formation of 3 may be rationalized in terms of stereoelectronically controlled cleavage of the conjugate base 17- of the tetrahedral intermediates. The rate of the conformational change of 17- into 18- and the equilibrium constant between these conformers are proposed to be the major factors affecting the reaction pattern.

Synthesis and deprotection of cyclic oxalate

As a new protective group for diols, cyclic oxalates [trans-1,2-cyclo-hexane diol 1,2-oxalate (1), 1,2:5,6-di-O-isopropylidene-D-mannitol 3,4-oxalate (2) and 1,2-propanediol 1,2-oxalate (3)] were synthesized by using oxalyl chloride, ethyloxalyl chloride,

Formation of cyclic carbonates in the reactions of 1,2-glycols with oxalyl chloride

Oxalyl chloride reacts with a wide range of 1,2-glycols in the presence of triethylamine to produce 1,3-dioxolan-2-ones together with 1,4-dioxane-2,3-diones; the ratio of the products largely depends on the structure of the 1,2-glycol. The formation of the cyclic carbonates may be rationalized in terms of stereoelectronically controlled cleavage of the tetrahedral intermediates.

Preparation and reaction of cyclic oxalate of diols

Cyclic oxalates were efficiently prepared by the reaction of diols with ethyl oxalyl chloride in the presence of triethylamine. They were stable under acidic conditions but cleaved to diols under basic conditions.