Phenol → Phenyl benzoate

HRID 861680Notes

Reaction equation

HRID 861680 reaction equation
[C:1]([O:9][CH3:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]1(O)[CH:16]=[CH:15]C=[CH:13][CH:12]=1>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].CO>[C:1]([O:9][C:10]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 996PhenolHCID 7150Methyl Benzoate

Product 1

HCID 7169Phenyl benzoateYield 74%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
190 °C

Procedure

A Claisen head was attached to a flask having an internal volume of 1000 ml, and 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 benzoate 100 g (735 mmole), phenol 553 g (5876 mmole) and titanium tetraisopropoxide 2.1 g (7.4 mmole). The contents were reacted with stirring at 190° C. in a bath. The reaction was conducted at atmospheric pressure, and the methanol thus produced was removed together with phenol. After reacting for 4 hours, excess phenol was distilled at atmospheric pressure. The remaining phenol and methyl benzoate were distilled under vacuum to obtain phenyl benzoate. The boiling point was 140° C./4mmHg. The yield was 108 g (74% yield in terms of methyl benzoate).

Workup

  1. customA Claisen head was attached to a flask
  2. customwas attached to the Claisen head via a condenser
  3. customThe contents were reacted
  4. customwas removed together with phenol
  5. distillationexcess phenol was distilled at atmospheric pressure
  6. distillationThe remaining phenol and methyl benzoate were distilled under vacuum

Sources & evidence

ORD record
ord-cdafe4eb4df8403c95ee1996fcedac10
Source dataset
uspto-grants-1998_02
Patent number
US05714627

Reaction notes

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