Phosphoric Acid → 2,6-Di-tert-butyl-4-methylphenol

HRID 1579081Notes

Reaction equation

[CH3:1][C:2](=[CH2:4])[CH3:3].P(=O)(O)(O)O.C1C(O)=CC=C(C)C=1.[C:18]([C:22]1[C:27]([OH:28])=[CH:26][CH:25]=[C:24]([CH3:29])[CH:23]=1)([CH3:21])([CH3:20])[CH3:19]>>[C:2]([C:26]1[C:27]([OH:28])=[C:22]([C:18]([CH3:20])([CH3:19])[CH3:21])[CH:23]=[C:24]([CH3:29])[CH:25]=1)([CH3:3])([CH3:1])[CH3:4]

Participants

Reactant 4

HCID 1004Phosphoric Acid

HCID 2879P-Cresol

HCID 8255Isobutylene

HCID 170042-tert-Butyl-4-methylphenol

Product 1

HCID 314042,6-Di-tert-butyl-4-methylphenol

Procedure

Approximately 1000 grams of the above described steam distilled reaction mixture was realkylated in a suitable reactor, by the addition of about 270 grams of isobutylene in the presence of a small amount of phosphoric acid and at a temperature of around 60°C, whereby practically all of the p-cresol in said mixture and around 90% of the mono-tert-butyl-p-cresol were realkylated to form additional 2,6-di-tert-butyl-p-cresol, thus producing a reacted mixture showing the following analysis:

Workup

distillationdistilled
customreaction mixture

Sources & evidence

ORD record: ord-b3b4a43e162e448e85bc512468005f1a
Source dataset: uspto-grants-1976_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03940451

Reaction notes

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