Reaction between 2,6-Di-t-butyl-p-cresol and Bromine

Abstract

Vol. 75 reflux six hours and decomposed with 10 cc. of 5% acetic acid, and the ether solution was washed with aqueous sodium bicarbonate, dried and evaporated in nitrogen. The dark residue was taken up in 5 cc. of boiling benzene, cooled and filtered to give 0.35 g. of crude 1,4,9-trihydroxy-9-phenyl-2,3-benzofluorene as a brown solid, m.p. 222-226°( dec.) (other specimens melted as low as 185°), soluble in alkali. The substance was converted to 4-hydroxy-9phenyl-2,3-benzo-l-isofluorenone in ten minutes by acetic acid at 100°. 9-Hydroxy-9-phenyl-2,3-benzofluorene-1,4-quinone, obtained by oxidation of the hydroquinone in ether with silver oxide, formed bright orange-yellow prisms from ether, m.p. 193-194°. The compound gave a pink solution in alcoholic alkali, a greenish-yellow vat and a dark olive solution in sulfuric acid. The ultraviolet and visible absorption maxima in ethanol solution lay at 258 µ (log t 4.34), 308 (3.86) and 417 (3.41).

The First Tetra(meso-аryl)porphyrin with Isobornyl Substituents

“…In the 1 H NMR spectrum of compound 3 the signals corresponding to pyrrolic H β protons of each of the four atropoisomers are observed; a small splitting is seen also for the signals of H 14 , H 16 and OH protons (Figure 1). In addition, a broadening of the signals of the other protons could also be due to small deviations of the spectral characteristics of different atropoisomers.…”

“…[14] Tetrapyrrole condensation with the aldehyde 2 was carried out by a procedure similar to the synthesis of tetra(mesophenyl)porphine -in boiling propionic acid at large dilution with following slow oxidation by atmospheric oxygen. [15] The structure of the obtained porphyrin 3 was confirmed by NMR, UV-vis and IR spectroscopy and mass spectrometry.…”

Synthesis of Vitamin E Novel Analogues as Anti-Cancer Compounds

“…T-butyl alcohol was used as the solvent instead of acetic acid by Coppinger et al (28), in their preparation of 2, 6-di-t-butyl-4-formylphenol. Bromine (37 mL, 2 equivalents) was added dropwise with mechanical stirring over two hours.…”

Synthesis of organophosphorus derivatives of 2,6‐di‐tert‐butyl‐4‐methylphenol

“…However, the methods for synthesis of such compounds are rather complicated and require rigid conditions [2][3][4][5][6]. In this work, we propose convenient procedures for synthesis of a series of ionol phosphorus derivatives with one, two, or three phosphorus-containing groups, starting from the readily accessible 3,5-di-tert-butyl-4-hydroxybenzaldehyde 1 prepared by the procedure described in [7] and trimethylsilyl esters of trivalent phosphorus acids, which are well known as unique organophosphorus synthons [8][9][10]. In the present study, we found that various trimethylsilyl esters of trivalent phosphorus acids react with aldehyde 1 and its derivatives under mild conditions to form new phosphorus-containing sterically hindered phenols.…”