Phenol → 4-(Triphenylmethyl)phenol

HRID 1856364Notes

Reaction equation

HRID 1856364 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]1([C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[C:8]1([C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:4]2[CH:5]=[CH:6][C:1]([OH:7])=[CH:2][CH:3]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 996PhenolHCID 6457Triphenylcarbinol

Product 1

HCID 704224-(Triphenylmethyl)phenolYield 75.8%

Conditions

Temperature
100 °C

Procedure

75.2 g (0.8 mol) of phenol and 52 g (0.2 mol) of triphenylcarbinol were boiled by heating on an oil bath and the resulting water was gradually removed together with excess phenol. When generation of water stopped, the reaction mixture was cooled to about 100° C. by allowing it to stand. Thereafter 2 g of zinc chloride was added and the mixture was heated to 130° to 140° C. whereupon white crystals rapidly precipitated. After heating for 30 minutes, the mixture was allowed to cool and 100 ml of methanol was added thereto, and the crystals were separated by filtration to obtain 51 g of p-triphenylmethylphenol having a melting point of 293° to 295° C.

Workup

  1. temperatureby heating on an oil bath
  2. customthe resulting water was gradually removed together with excess phenol
  3. additionThereafter 2 g of zinc chloride was added
  4. temperaturethe mixture was heated to 130° to 140° C. whereupon white crystals
  5. customrapidly precipitated
  6. temperatureAfter heating for 30 minutes
  7. temperatureto cool
  8. addition100 ml of methanol was added
  9. customthe crystals were separated by filtration

Sources & evidence

ORD record
ord-b0c167644ebb4c688902f9b91851d4e1
Source dataset
uspto-grants-1980_08
Patent number
US04219219

Reaction notes

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