4832. 5-(Hydroxymethyl)-2-furaldehyde

Nomenclature

CAS number: 67-47-0
5-(Hydroxymethyl)-2-furancarboxaldehyde; 5-(hydroxymethyl)-2-furancarbonal; 5-(hydroxymethyl)-2-furfural; HMF; 5-hydroxymethyl-2-formylfuran.
C6H6O3; mol wt 126.11.
C 57.14%, H 4.80%, O 38.06%.

Description and references

Prepn from the fructose portion of the sugar molecule in 57% yield: Haworth, Jones, J. Chem. Soc. 1944, 667; Haworth, Wiggins, GB 591858 (1947); GB 600871 (1948). Improved process: Garber, Jones, US 2929823 (1960 to Merck & Co.). Purification: Jones, Lange, US 2994645 (1961 to Merck & Co.). Outline of process using cornstarch, glucose and sucrose as raw materials: Medwick, Chem. Eng. News 75 (Sept. 11, 1961). Prepn from molasses: Jones, Lange, US 3066150 (1962 to Merck & Co.); Hales et al., US 3071599 (1963 to Atlas Chem.).

Chemical structure

Properties

Needles from ether + petr ether, mp 31.5°. Avoid contact with eyes. Produces harmless yellow stains on skin. Odor of chamomile flowers. Very slightly volatile with steam (as compared with furfural). d425 1.2062. bp0.02 110°. nD18 1.5627. uv max: 283 nm. Heat of combustion: 665 kcal/mol. Freely sol in water, methanol, ethanol, acetone, ethyl acetate, dimethylformamide. Sol in ether, benzene, chloroform. Less sol in carbon tetrachloride. Sparingly sol in petr ether. Keep protected from light and air.

Use

In the synthesis of dialdehydes, glycols, ethers, aminoalcohols, acetals. Aq acid catalyzes ring opening.