Phenyl 3,5-di-tert-butyl-2-hydroxybenzoate

Abstract

The title mol­ecule, C21H26O3, has a six-membered planar carbon ring as the central core, substituted at position 1 with phen­oxy­carbonyl, at position 2 with hy­droxy and at positions 3 and 5 with tert-butyl groups. The structure shows two independent but very similar mol­ecules within the asymmetric unit. For both independent mol­ecules, the ester carboxyl­ate group is coplanar with the central core, as reflected by the small C—C—O—C torsion angles [179.95 (17) and 173.70 (17)°]. In contrast, the phenyl substituent is almost perpendicular to the carboxyl­ate –CO2 fragment, as reflected by C—O—C—C torsion angles, ranging from 74 to 80°. The coplanarity between the central aromatic ring and the ester carboxyl­ate –CO2– group allows the formation of an intra­molecular hydrogen bond, with O⋯O distances of 2.563 (2) and 2.604 (2) Å.

Theoretical and experimental characterization of a novel pyridine benzimidazole: suitability for fluorescence staining in cells and antimicrobial properties

“…Synthesis of the precursor phenyl-3,5-di-tert-butyl-2-hydroxibenzoate (B1). The synthesis was prepared according to Benisvy et al 44,45 The 3,5-di-tert-butyl-salicylic acid (20 mmol), N,N 0dicyclohexylcarbodiimine (28.8 mmol) and phenol (30 mmol) were added to dry THF (120 mL) and stirred for 4 days under a nitrogen atmosphere at room temperature. The colorless oil was purified by a column in pentane and recrystallized from chloroform.…”

“…The cationic or anionic form of B2 and L2 maintain the same conformation of the neutral form due to the intramolecular hydrogen bond, 45,46 with an increment in the -HCQN-distance for L2 charged forms,. 32 In the same way, the calculated frequencies for B2 are in good agreement with the values observed in the FT-IR spectra for the most important functional groups in similar compounds.…”