Phenol → Phenyl 4-methylbenzoate

HRID 861677Notes

Reaction equation

HRID 861677 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:3][CH:2]=1.[C:12]1(O)[CH:17]=[CH:16]C=[CH:14][CH:13]=1>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([C:7]([O:9][C:10]2[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=2)=[O:8])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 996PhenolHCID 7455Methyl 4-methylbenzoate

Product 1

HCID 219444Phenyl 4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Conditions

Temperature
190 °C

Procedure

A thermometer and Claisen head were attached to a three-necked flask having an internal volume of 500 ml. A receiver having a gage was attached to the Claisen head via a condenser to make a distillation apparatus. Into this apparatus were charged methyl p-toluate 75 g (0.50 mole), phenol 376 g (4.0 mole) and titanium tetraisopropoxide 1.42 g (5.0 mmole). The contents were reacted with stirring in a 190° C. bath. The reaction was conducted at atmospheric pressure for six hours while removing methanol produced in the reaction. Then, the temperature of the bath was elevated to 196° to 198° C., and phenol was removed by distillation in an amount of as much as 150 g. The remaining phenol and methyl p-toluate were removed by distilling under vacuum (85 mmHg). Then, the vacuum pressure was decreased to obtain phenyl p-toluate. The boiling point was 183° to 185° C./18 mmHg, and the product was a slightly yellow colored white solid. The yield was 72.98 g, (69% in terms of methyl p-toluate). The melting point was 74° to 76° C.

Workup

  1. customA thermometer and Claisen head were attached to a three-necked flask
  2. customwas attached to the Claisen head via a condenser
  3. customThe contents were reacted
  4. customwhile removing methanol
  5. customproduced in the reaction
  6. customwas elevated to 196° to 198° C.
  7. customphenol was removed by distillation in an amount of as much as 150 g
  8. customThe remaining phenol and methyl p-toluate were removed
  9. distillationby distilling under vacuum (85 mmHg)

Sources & evidence

ORD record
ord-8d325b4c92ec4e5dbf8f30ca402e01b3
Source dataset
uspto-grants-1998_02
Patent number
US05714627

Reaction notes

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