Phenol → 2,4,6-Tri-tert-butylphenol

HRID 1709801

Reaction equation

HRID 1709801 reaction equation
C1(O)C=CC=CC=1.P(=O)(O)(O)O.[CH3:13][C:14](=[CH2:16])[CH3:15].[C:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[OH:27])([CH3:20])([CH3:19])[CH3:18].[C:28](C1C=CC(O)=CC=1)([CH3:31])([CH3:30])[CH3:29].[C:39]([C:43]1[CH:48]=[C:47]([C:49]([CH3:52])([CH3:51])[CH3:50])[CH:46]=[CH:45][C:44]=1[OH:53])([CH3:42])([CH3:41])[CH3:40]>C(O)(=O)C>[C:14]([C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:17]([CH3:19])([CH3:18])[CH3:20])[C:22]=1[OH:27])([CH3:15])([CH3:13])[CH3:16].[C:39]([C:43]1[CH:48]=[C:47]([C:49]([CH3:52])([CH3:51])[CH3:50])[CH:46]=[C:45]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:44]=1[OH:53])([CH3:42])([CH3:41])[CH3:40]

Participants

9

Reactant 6

HCID 996Phenol2×HCID 1004Phosphoric AcidHCID 69232-Tert-ButylphenolHCID 73112,4-Di-tert-butylphenolHCID 73934-tert-ButylphenolHCID 8255Isobutylene

Product 2

HCID 129022,4,6-Tri-tert-butylphenolHCID 314052,6-Di-tert-butylphenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A 100 ml-autoclave was charged with 28 g of phenol, 4 g of phosphoric acid and 20 g of acetic acid, and heated at 120° C. Thereto was gradually added 34 g of isobutylene and the mixture was stirred at 120° C. for 3 hours. The reaction mixture consisted of 1.0% of phenol, 14% of 2-tert-butylphenol, 11% of 4-tert-butylphenol and 74% of 2,4-di-tertbutylphenol, when analyzed with gas chromatography as a % area. 2,6-Di-tert-butylphenol and 2,4,6-tri-tert-butylphenol were not formed. Phosphoric acid and acetic acid were removed by washing with water. Distillation at 170° C. gave 44 g of 2,4-di-tert-butylphenol. Each spectra of NMR, MS and IR of the objective compound was identical with those of the standard compound.

Sources & evidence

ORD record
ord-b1318eb400da47818225dc9005546c14
Source dataset
uspto-grants-1990_08
Patent number
US04950810

Linked notes

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