2,6-Di-tert-butylphenol → 4,4'-Dihydroxybiphenyl

HRID 329489Notes

Reaction equation

HRID 329489 reaction equation
C(C1C=CC=C(C(C)(C)C)C=1O)(C)(C)C.C([C:20]1[CH:21]=[C:22]([C:31]2[CH:36]=[C:35](C(C)(C)C)[C:34]([OH:41])=[C:33](C(C)(C)C)[CH:32]=2)[CH:23]=[C:24](C(C)(C)C)[C:25]=1[OH:26])(C)(C)C>>[CH:23]1[C:22]([C:31]2[CH:36]=[CH:35][C:34]([OH:41])=[CH:33][CH:32]=2)=[CH:21][CH:20]=[C:25]([OH:26])[CH:24]=1

Participants

3

Reactant 2

HCID 314052,6-Di-tert-butylphenolHCID 671854,4'-Bis(2,6-di-tert-butylphenol)2×

Product 1

HCID 71124,4'-Dihydroxybiphenyl

Procedure

If a mixture of 2,6-di-t-butylphenol and 3,3',5,5'-tetra-t-butyl-4,4'-diphenoquinone, or a mixture thereof with 3,3',5,5'-tetra-t-butyl-4,4'-dihydroxybiphenyl is treated under the reaction conditions described above concerning catalyst, solvent, temperature and time, the reaction for the synthesis of 3,3',5,5'-tetra-t-butyl-4,4'-dihydroxybiphenyl and that for the dealkylation of this compound will proceed in a balanced and efficient way, thereby allowing p,p'-biphenol to be produced in a satisfactory yield. Stated more specifically, any 3,3',5,5'-tetra-t-butyl-4,4'-diphenoquinone that may be formed on account of excessive oxidation of 3,3',5,5'-tetra-t-butyl 4,4'-dihydroxybiphenyl is reduced with 2,6-di-t-butylphenol to ensure efficient production of 3,3',5,5'-tetra-t-butyl-4,4'-dihydroxybiphenyl therefrom. In addition, the so produced 3,3',5,5'-tetra-t-butyl-4,4'-dihydroxybiphenyl is converted efficiently to p,p'-biphenol by dealkylation.

Workup

  1. customthe reaction

Sources & evidence

ORD record
ord-7b8de60c8a1048e981a0c0f9cadc7724
Source dataset
uspto-grants-1990_01
Patent number
US04891453

Reaction notes

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