A Simple and Efficient Synthesis of Ethyl and Methyl Glyoxylate

References

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• Heating ethyl diethoxyacetate 3 with phosphorus pentoxide directly, lead to variable yields of ethyl glyoxylate 1, c.f. ref. 10
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• Methyl glyoxylate 2 has been prepared in 94% yield on twice the scale described here. A.B. Holmes and J. Thompson, personal communication
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• The reaction mixture at this stage may be conveniently stored in a refrigerator under argon indefinitely, and distilled to yield glyoxylic ester as required. A.B. Holmes and J. Thompson, personal communication
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• The 1H n.m.r. data were obtained with freshly distilled glyoxylate, and show that it is almost entirely aldehyde. Presumably the pure aldehyde polymerises on standing, but in such a way that it still participates in, for example, a Wittig reaction. The pure aldehyde may be regenerated by further distillation from phosphorus pentoxide; cf. ref. 9
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