Phenol → 4,4'-Bis(2,6-di-tert-butylphenol)

HRID 329494Notes

Reaction equation

[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[C:13]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:18]=1[OH:27])([CH3:16])([CH3:15])[CH3:14]>>[C:13]([C:2]1[CH:3]=[C:4]([C:21]2[CH:22]=[C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:18]([OH:27])=[C:19]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:20]=2)[CH:5]=[C:6]([C:19]([CH3:23])([CH3:20])[CH3:18])[C:1]=1[OH:7])([CH3:16])([CH3:15])[CH3:14]

Participants

Reactant 3

HCID 996Phenol

HCID 1118Sulfuric Acid

HCID 314052,6-Di-tert-butylphenol

Product 1

HCID 671854,4'-Bis(2,6-di-tert-butylphenol)

Procedure

A portion (10.0 g) of this reaction solution was used in the subsequent process. Phenol (20 g) and sulfuric acid (0.04 g) were added to 10.0 g of reaction solution (1) not only for neutralizing the base in the reaction system but also to render the reaction solution acidic (pH, 1). Thereafter, the following two reactions were performed in one step at 180° C. over a period of 6 hours: a redox reaction in which the unreacted 2,6-di-t-butylphenol and 3,3',5,5'-tetra-t-butyl-4,4'-diphenoquinone were reacted to produce 3,3',5,5'-tetra-t-butyl-4,4'-dihydroxybiphenyl; and a reaction in which 3,3',5,5'-tetra-t-butyl-4,4'-dihydroxybiphenyl was dealkylated into p,p'-biphenol.

Workup

customwere reacted

Sources & evidence

ORD record: ord-4099e6de8eb04bd6a87ed0f997e3cacd
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04891453

Reaction notes

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