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This reagent was originally prepared by Conrad Willgerodt [3] by reacting iodobenzene with a mixture of acetic acid and peracetic acid: [4] [5] C 6 H 5 I + CH 3 CO 3 H + CH 3 CO 2 H → C 6 H 5 I(O 2 CCH 3) 2 + H 2 O. PIDA can also be prepared from iodosobenzene and glacial acetic acid: [5] C 6 H 5 IO + 2 CH 3 CO 2 H → C 6 H 5 I(O 2 CCH 3) 2 ...
Iodobenzene is commercially available, or it can be prepared in the laboratory from aniline via the diazotization reaction. In the first step, the amine functional group is diazotized with hydrochloric acid and sodium nitrite. Potassium iodide is added to the resultant phenyldiazonium chloride, causing nitrogen gas to evolve. The product is ...
Iodobenzoic acids are any of three organic compounds with the formula IC 6 H 4 COOH, consisting of a carboxylic acid group and an iodine atom bonded to a central benzene ring. They can be considered as iodinated derivatives of benzoic acid, or as carboxylated variants of iodobenzene.
In hot water (or, in Willgerodt's original preparation, steam distillation), iodosobenzene instead disproportionates to iodoxybenzene and iodobenzene: [7] 2 PhIO → PhIO 2 + PhI. 2-Iodobenzoic acid reacts with oxone [8] or a combination of potassium bromate and sulfuric acid to produce the insoluble λ 5 ‑iodane 2-iodoxybenzoic (IBX) acid. [9]
The reaction can also be carried out under mildly acidic conditions by way of the same intermediate using a hypervalent iodine compound in aqueous solution. [1] An example published in Organic Syntheses is the conversion of cyclobutanecarboxamide, easily synthesized from cyclobutylcarboxylic acid, to cyclobutylamine. [2]
Oxidative phenol coupling has been used for the synthesis of alkaloids related to morphine. For instance, the reaction has been employed to transform reticuline derivatives into salutaridine derivatives in a single, presumably biomimetic, step. Yields of reactions of this type tend to be low, however. [13] (11)
The synthesis of 2-iodobenzoic acid via the diazotization of anthranilic acid is commonly performed in university organic chemistry labs. One of its most common uses is as a precursor for the preparation of IBX and Dess–Martin periodinane , both used as mild oxidants.
The symmetrical structure [clarification needed] of α-phenyl propanamide does not change after Hofmann reaction. In the synthesis of gabapentin, beginning with the mono-amidation of 1,1-cyclohexane diacetic acid anhydride with ammonia to 1,1-cyclohexane diacetic acid mono-amide, followed by a Hofmann rearrangement [12]