The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Condensation of benzaldehyde with bromoacetonitrile》. Authors are Vul’fson, N. S.; Vinograd, L. Kh..The article about the compound:3-Hydroxy-3-phenylpropanenitrilecas:17190-29-3,SMILESS:N#CCC(O)C1=CC=CC=C1).Computed Properties of C9H9NO. Through the article, more information about this compound (cas:17190-29-3) is conveyed.
To a refluxing solution of 21.3 g. BzH, 32 ml. C6H6, and 8 ml. Et2O containing 18 g. activated Zn dust there was added in 0.5 hr. 24 g. BrCH2CN. After refluxing 2 hrs. the cooled mixture was stirred 1 hr. with 120 ml. 10% H2SO4, filtered, separated, the organic layer extracted with 10% H2SO4 and H2O, and the combined aqueous layers extracted with C6H6 and combined with the original organic layer. Distillation gave 14.2 g. PhCH(OH)CH2CN, b4-5 147-51°. This shaken with 12% H2O2 in the presence of 1 drop of NaOH and little EtOH gave the corresponding amide, m. 120° (from EtOH). Refluxing the nitrile with 4N NaOH gave 63.6% PhCH:CHCO2H.
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Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics