Phenol → 4-(1,1-diphenylethyl)phenol

HRID 1856366Notes

Reaction equation

HRID 1856366 reaction equation
[C:1]1([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>>[C:1]1([C:7]([C:18]2[CH:19]=[CH:20][C:15]([OH:21])=[CH:16][CH:17]=2)([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 996PhenolHCID 6101p-Toluenesulfonic acid2×HCID 107401,1-DiphenylethyleneHCID 516892Sodium Bicarbonate

Product 1

HCID 2450614-(1,1-diphenylethyl)phenol

Procedure

1,1-Diphenylethylene and phenol in an excess amount were heated in an oil bath at 140° to 150° C. for 1 hour in the presence of p-toluenesulfonic acid. After being allowed to cool, p-toluenesulfonic acid was neutralized using sodium hydrogencarbonate and the excess phenol was then removed by steam distillation to obtain p-(1,1-diphenylethyl)phenol. The resulting phenol was then subjected to carboxylation by the Kolbe reaction according to the process described in Synthesis Example 1 to obtain Compound (4) which was then converted into the zinc salt by the same process as that described in Synthesis Example 2.

Workup

  1. temperatureto cool
  2. customthe excess phenol was then removed by steam distillation

Sources & evidence

ORD record
ord-9a33e9db65c041ca84efa519609bf79b
Source dataset
uspto-grants-1980_08
Patent number
US04219219

Reaction notes

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