Phenol → 3-[1-(4-Hydroxyphenyl)-isopropyl]phenol

HRID 1462659

Reaction equation

HRID 1462659 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)[OH:9].O[C:14]1[CH:15]=[C:16]([C:20]([CH3:23])([CH3:22])O)[CH:17]=[CH:18][CH:19]=1>C1(C)C=CC=CC=1>[OH:7][C:1]1[CH:6]=[C:5]([C:20]([C:16]2[CH:17]=[CH:18][C:19]([OH:9])=[CH:14][CH:15]=2)([CH3:23])[CH3:22])[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996Phenol2×HCID 1118Sulfuric AcidHCID 4581423-(2-Hydroxypropan-2-yl)phenol

Product 1

HCID 6882893-[1-(4-Hydroxyphenyl)-isopropyl]phenolYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 1335 grams (14.2 moles) of phenol, 450 ml. of 75% aqueous sulfuric acid and 1800 ml. of toluene was stirred at room temperature while a solution of 450 grams (2.9 moles) of 3-hydroxyphenyldimethylcarbinol in 890 grams (9.5 moles) of phenol and 1800 ml. of toluene was added over three hours. The reaction mixture was stirred at room temperature for four hours and the aqueous layer was separated and discarded. The organic layer was washed twice with water, once with 10% sodium bicarbonate solution and again with water. Toluene and excess phenol were removed by vacuum distillation and the residue was recrystallized from toluene. There was obtained 371 grams (55% of theoretical) of the desired 2-(3-hydroxyphenyl)-2-(4-hydroxyphenyl)propane.

Workup

  1. customthe aqueous layer was separated
  2. washThe organic layer was washed twice with water, once with 10% sodium bicarbonate solution and again with water
  3. customToluene and excess phenol were removed by vacuum distillation
  4. customthe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-554cd87da3cd43c08592993d77fc3552
Source dataset
uspto-grants-1984_07
Patent number
US04460798

Linked notes

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