The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Fermentation products of wheat germ. (a) Identification of methoxy- and 2,6-dimethoxy-p-benzoquinone. (b) Infrared absorption of some quinones and 1,2-dicarboxyl compounds》. Authors are Cosgrove, D. J.; Daniels, D. G. H.; Whitehead, J. K.; Goulden, J. D. S..The article about the compound:1-(Furan-2-yl)propan-1-onecas:3194-15-8,SMILESS:O=C(C1=CC=CO1)CC).Synthetic Route of C7H8O2. Through the article, more information about this compound (cas:3194-15-8) is conveyed.
The compounds isolated by Vuataz (C.A. 44, 7896g) from wheat germ fermented with baker’s yeast have been identified as methoxy-p-benzoquinone and 2,6-dimethoxy-p-benzoquinone. 1-(2-Furyl)acetone (I) was prepared in 33% yield by hydrolyzing and decarboxylating the compound formed by condensing MeCHClCO2Et (Frankland and Garner, C.A. 8, 2361) and furfuraldehyde (Darzens, Compt. rend. 142, 214(1906)). I (15 g.) was added to 13.6 g. SeO2 in 75 ml. dioxane and 2.5 ml. H2O at 50°, the mixture refluxed 4 hrs., the Se filtered off, the solvent removed in vacuo from the filtrate, and the residue chromatographed in CHCl3 on Al2O3; elution with CHCl3 gave 2.9 g. 1-(2-furyl)-1,2-propanedione (II), b16 94-5°, m. 64-5°. Furan (46 g.) acylated at 10-15° with 102 g. (EtCO)2O and 1.2 ml. HI (d. 1.70) (Hartough and Kosak, C.A. 41, 1661d), gave 43% 2-propionylfuran (Gilman and Calloway, C.A. 27, 5738), which was oxidized with SeO2 as before; the reaction was still incomplete after 5.5 hrs., refluxing, but 1.4 g. II, m. 60-1°, was ultimately obtained. 2-Methylfuran (Kizhner, C.A. 26, 5299) acylated at 0-10° by the use of HI (d. 1.70) and worked up as above gave 5-methylfurylglyoxal, b20 109-10°. Infrared spectra of some p-benzoquinones, glyoxals, and 1,2-diketones are presented.
The article 《Fermentation products of wheat germ. (a) Identification of methoxy- and 2,6-dimethoxy-p-benzoquinone. (b) Infrared absorption of some quinones and 1,2-dicarboxyl compounds》 also mentions many details about this compound(3194-15-8)Synthetic Route of C7H8O2, you can pay attention to it, because details determine success or failure
Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem