The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Interchange of alcohol radicals in esters. II》. Authors are Shimomura, Akira; Cohen, J. B..The article about the compound:4-(((1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl)oxy)-4-oxobutanoic acidcas:77341-67-4,SMILESS:CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)CCC(O)=O).Quality Control of 4-(((1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl)oxy)-4-oxobutanoic acid. Through the article, more information about this compound (cas:77341-67-4) is conveyed.
cf. C. A. 16, 2502. The acid nature of an alkyl ester seems to promote the interchange of groups. The introduction of the following groups generally helps the reaction: Ph, Ac, AcO, PhO, CO2H, NO2. Halogens do not materially affect the interchange. In some cases a double bond does. Most of the esters of α-ketonic acids undergo interchange, due, undoubtedly, to the presence of the CO group in the α-position to the CO2H group. The HO group is not favorable to the interchange. In the case of esters of BzH derivatives, o- and p-compounds behave similarly but differ from the m-compound The following new esters are described: l-Menthyl acetylpyruvate, b12 185-92°, [α]D1872.3° ; monoacetylmalonate, long needles, m. 58°, [α]D19 -77.5°; phenoxy-malonate, microneedles, m. 96° [α]D17-55.5°; ethoxymethylevemalonate, b10 215-21°, [α]D20- ; hydrogen succinate, prisms, m. 57-9°, [α]D17 -61.0°.
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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem