Phenol → Phenol, 4-[1-(4-aminophenyl)-1-methylethyl]-

HRID 1758585Notes

Reaction equation

HRID 1758585 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(O)C=CC=CC=1.[C:15]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)([CH3:17])=[CH2:16]>Cl.OC1C=CC(C(C2C=CC(O)=CC=2)(C)C)=CC=1>[OH:24][C:21]1[CH:22]=[CH:23][C:18]([C:15]([C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)([CH3:17])[CH3:16])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 6115Aniline2×HCID 584247p-Isopropenylphenol6×

Product 1

HCID 11148864Phenol, 4-[1-(4-aminophenyl)-1-methylethyl]-Yield 378.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6623Bisphenol ACatalyst

Conditions

Temperature
180 °C

Procedure

Ten grams of aniline was added to a mixture consisting of 13.0 g of phenol, 3.4 g of p-isopropenyl phenol monomer, 8.5 g of a linear dimer of p-isopropenyl phenol, 1.1 g of a linear trimer of p-isopropenyl phenol and 0.8 g of a linear tetramer and higher polymers of p-isopropenyl phenol (1.05 mole of aniline per mole of the p-isopropenyl phenol monomeric unit). The mixture was stirred at 180° C. Then, 0.2 g of 10% hydrochloric acid (0.0053 mole per mole of the p-isopropenyl phenol monomeric unit) was added, and the reaction was performed for 2 hours. Gas-chromatographic analysis of the reaction mixture showed that 0.38 g of bisphenol A and 21.8 g (yield 93%) of 2-(4'-hydroxyphenyl)-2-(4'-aminophenyl)-propane were formed.

Sources & evidence

ORD record
ord-6d9aeae834bd4baaa4db52a744edef25
Source dataset
uspto-grants-1983_02
Patent number
US04374272

Reaction notes

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