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US 8,710,250 B2Granted
Conversion of 5-(chloromethyl)-2-furaldehyde into 5-methyl-2-furoic acid and derivatives thereof
AssigneeXf Technologies B.V.
InventorsPeter Mikochik, Aviad Cahana
Life of this patent
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Abstract
The present invention concerns the synthesis of 5-methyl-2-furoic acid, including ester, amide, and thioester derivatives of such from 5-(chloromethyl)-2-furaldehyde (CMF). The molecules so prepared are useful as intermediates for pharmaceutical, food, and fragrance molecules; as well as fuel or fuel additives.
Claims13
A method for the synthesis of an output consisting of one or more of:
- an ester of 5-methyl-2-furoic acid, an amide of 5-methyl-2-furoic acid, and a thioester of 5-methyl-2-furoic acid, from a precursor consisting of 5-methyl-furaldehyde with one hydrogen of the 5-methyl group replaced with one of chloride, fluoride, bromide, iodide, p-toluenesulfonate, methanesulfonate, trifluoroacetate, phenoxy, hydroxy, or ammonium, the method comprising:
- (a) contacting the precursor, a base, an organic solvent, a catalyst, and a reactive nucleophile in a reaction vessel at a temperature of from about −78 degrees C. to about 150 degrees C., such that molecules of the output are produced;
- (b) separating the molecules of the output by extraction with a hydrophobic solvent, or else by chromatography, distillation, sublimation, or precipitation;
- wherein the catalyst is one or more of:
- (1) a N-heterocyclic carbene, (2) a salt of a N-heterocyclic carbene, (3) cyanide, (4) chloride, (5) bromide, (6) iodide, (7) thiazolium, (8) 1,2,4-triazolium, (9) imidazolium, (10) tetrazolium ring system.
2 more elements
Dependencies are inferred from the claim text.