The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Hydrogenation of 3-methylphthalide》. Authors are Kolsaker, Per.The article about the compound:cis-Cyclohexane-1,2-dicarboxylic acidcas:610-09-3,SMILESS:O=C([C@H]1[C@@H](C(O)=O)CCCC1)O).Safety of cis-Cyclohexane-1,2-dicarboxylic acid. Through the article, more information about this compound (cas:610-09-3) is conveyed.
The catalytic hydrogenation, at 20° and 1 atm., of 3-methylphthalide (I) gave 60% cis-3-methylhexahydrophthalide (II), b10 130-1°, n20D 1.4748, d20 1.0595 (oxidized by NaOBr to cyclohexane-cis-1,2-dicarboxylic acid, m. 189-93°), and 40% trans-2-ethylcyclohexanecarboxylic acid (III), m. 35-7°, b10 134-5°, n20D 1.468, d20 1.015 (p-bromophenacyl ester m. 71-2°). With HI and yellow P, I gave 2-ethylbenzoic acid, b0.15 49-52°, n20D 1.5300, d20 1.462, while II gave a good yield of cyclo-C6H11CHIMe. Catalytic hydrogenation of o-AcC6H4CO2H also gave I and III.
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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics