Synthesis of 5-nitro-2-furaldehyde diacetate

Preparation of 5-nitro-2-furaldehyde diacetate

Preparation of 5-nitro-2-furaldehyde diacetate

Preparation of 5-nitro-2-furaldehyde diacetate

A mixture of 143 grams acetic anhydride and 43.7 grams of fuming nitric acid (d=1.5 g/ml) is prepared at 0° C and a solution of 49.5 grams of 2-furaldehyde diacetate in 51 grams acetic anhydride is dropped in within 30-40 min, the temperature not being allowed to rise above —5° C. The mixture is stirred for 3 hours, then poured to ice and treated, with stirring, with the solution of 40 % sodium hydroxide until separation of an oil is complete. The aqueous layer is removed and to the oil an equal volume of pyridine is added cautiously in small portions, whereby the ring-opened intermediate is recyclized. After warming for some time and then dilution with 2-3 parts of ice-water by volume, the resulting precipitate is filtered off and washed with dilute acetic acid and then water until free from pyridine. Crude 5-nitro-2-furaldehyde diacetate (24.5 g, 40%; melting point 85° C) gives material, which melts at 92.5° C on recrystallization from ethanol. 5-Nitro-2-furaldehyde diacetate is converted into 5-nitro-2-furaldehyde by treating with sulfuric acid.

J. Amer. Chem. Soc, 52, 2550, 4165, 1930.

IUPAC Name

[acetyloxy-(5-nitrofuran-2-yl)methyl] acetate

InChI

InChI=1S/C9H9NO7/c1-5(11)15-9(16-6(2)12)7-3-4-8(17-7)10(13)14/h3-4,9H,1-2H3

InChI Key

HSXKWKJCZNRMJO-UHFFFAOYSA-N

Canonical SMILES

CC(=O)OC(C1=CC=C(O1)[N+](=O)[O-])OC(=O)C

Depositor-Supplied Synonyms

5-Nitro-2-furaldehyde diacetate, 2-(Diacetoxymethyl)-5-nitrofuran, 5-Nitrofurfurylidene diacetate, 92-55-7, 5-Nitro-2-furanmethanediol diacetate, Nitrofuraldehyde diacetate, 5-Nitrofurfural diacetate, 5-Nitro-2-furfural diacetate, 5-Nitro-2-furfuraldehyde diacetate, 5-Nitro-2-furanmethandiol diacetate, 5-Nitrofuraldehyde diacetate, 5-Nitro-2-furancarboxaldehyde diacetate, NSC 5411, (5-Nitrofuran-2-yl)methylene diacetate, (5-nitrofuran-2-yl)methanediyl diacetate, Methanediol, (5-nitro-2-furanyl)-, diacetate (ester), 5-nitro-2-furaldehydediacetate, CCRIS 1191, (acetyloxy)(5-nitrofuran-2-yl)methyl acetate, 5-Nitrofurfurylidene di(acetate), HSXKWKJCZNRMJO-UHFFFAOYSA-N, 2-FURANMETHANEDIOL, 5-NITRO-, DIACETATE, EINECS 202-166-1, 5-Nitro-2-furan methandiol diacetate, Methanediol, 1-(5-nitro-2-furanyl)-, 1,1-diacetate, BRN 0255089, AI3-23602, acetyloxy(5-nitro(2-furyl))methyl acetate, AC1Q5AZX, DSSTox_CID_946, Maybridge1_006444, UNII-7X0X1KNE3Q, 7X0X1KNE3Q, DSSTox_RID_75882, DSSTox_GSID_20946, 2-Furanmethanediol, diacetate, AC1L1O01, CHEMBL402463, SCHEMBL6550567, 5-Nitrofurfural Diacetyl Acetal, CTK3J4291, HMS559M20, HSXKWKJCZNRMJO-UHFFFAOYSA-, NSC5411, MolPort-000-145-640, NSC-5411, 2-(Diacetoxymethyl)-5-nitro-furane, Tox21_200727, AR-1G9104, SBB056636, STK325717, ZINC00056461, (5-nitro-2-furyl)methylene diacetate, AKOS000121509, LS-7549, MCULE-6183062905, NE26486, RTR-033616, CAS-92-55-7, NCGC00248811-01, NCGC00258281-01, AJ-09269, AK114183, AN-42605, ZB001656, [acetoxy-(5-nitro-2-furyl)methyl] acetate, TR-033616, FT-0620690, N0218, ST24020639, ST45021453, [acetyloxy-(5-nitro-2-furyl)methyl] acetate, (Acetyloxy)(5-nitro-2-furyl)methyl acetate #, [acetyloxy-(5-nitrofuran-2-yl)methyl] acetate, Methanediol, (5-nitro-2-furanyl)-, diacetate, 5-17-09-00324 (Beilstein Handbook Reference), I14-7528, T5662323, 3B3-028883, 58928-41-9, InChI=1/C9H9NO7/c1-5(11)15-9(16-6(2)12)7-3-4-8(17-7)10(13)14/h3-4,9H,1-2H3

Removed Synonyms

Methanediol, diacetate (ester), CID7097, 98355-36-3

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