Encyclopedia of Reagents for Organic Synthesis

3,3′,5,5′-Tetra-tert-butyldiphenoquinone

Osamu Niyomura, Shigeki Habaue

First published: 14 September 2012

https://doi.org/10.1002/047084289X.rn01487

Abstract

[2455-14-3]  C28H40O2  (MW 408.63)

InChI = 1S/C28H40O2/c1-25(2,3)19-13-17(14-20(23(19)29)26(4,5)6)18-15-21(27(7,8)9)24(30)22(16-18)28(10,11)12/h13-16H,1-
12H3

InChIKey = GQIGHOCYKUBBOE-UHFFFAOYSA-N

(oxidizing reagent for various oxidation reactions such as oxidative coupling of organometallic compounds, oxidative cross-
coupling between nitrones and alkynes, N-heterocyclic carbene-catalyzed oxidative esterification, amidation, and azidation of
aldehydes, Michael addition to α,β-unsaturated aldehydes)

Alternate Names: 3,3′,5,5′-tetra-tert-butyl-4,4′-dibenzoquinone; 3,3′,5,5′-tetra-tert-butyl-4,4′-diphenoquinone; 2,6-bis(1,1-

dimethylethyl)-4-[3,5-bis(1,1-dimethylethyl)-4-oxo-2,5-cyclohexadien-1-ylidene]-2,5-cyclohexadien-1-one; 2,6-bis(1,1-
dimethylethyl)-4-[3,5-bis(1,1-dimethylethyl)-4-oxo-2,5-cyclohexa-dien-1-ylidene]-2,5-cyclohexadien-1-one; 2,2′,6,6′-tetra-tert-
butyldiphenylquinone.

Physical Data: mp 246 °C,1 244−246 °C.2

Solubility: sol MeOH, EtOH, iPrOH, THF, acetone, AcOH, hexane; insoluble in water.

Form Supplied in: commercially available as a red to purple solid.

Preparative Method: synthesized by oxidation of 2,6-di-tert-butylphenol with oxygen gas in the presence of KOH in t-BuOH.1

Purification: recrystallization from EtOH.1

Handling, Storage, and Precautions: store away from oxidizing agents in dark and cool place in tightly sealed container; avoid
inhalation and contact with skin and eyes.

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