Acetic Acid → Phenyl acetate

HRID 1184951Notes

Reaction equation

HRID 1184951 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8](O)(=[O:10])[CH3:9].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:8]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 996PhenolHCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 31229Phenyl acetateYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Toluene (100 ml), phenol (8.94 g, 95 mmol) and acetic acid (6.05 g, 100 mmol) were added into a 200-ml flask in this order at room temperature and then p-toluenesulfonic acid monohydrate (2.85 g, 15 mmol) was charged thereto. The solution was gently heated and subjected to reflux dehydration for 3 to 5 hours. After reflux dehydration, the solution was cooled to around room temperature, added with triethylamine (2.40 g, 25 mmol) at room temperature, stirred and then added with silica gel. After continuing to stir for a while, the silica gel was filtered off. After the solvent of the filtrate was removed in vacuum distillation, phenyl acetate (11.64 g, 90%) was isolated in distillation.

Workup

  1. temperatureThe solution was gently heated
  2. temperatureto reflux dehydration for 3 to 5 hours
  3. temperatureAfter reflux dehydration
  4. temperaturethe solution was cooled to around room temperature
  5. additionadded with silica gel
  6. stirringto stir for a while
  7. filtrationthe silica gel was filtered off
  8. customAfter the solvent of the filtrate was removed in vacuum distillation

Sources & evidence

ORD record
ord-0beb6313c6064bd1b9129f81b5ada5dd
Source dataset
uspto-grants-2014_03
Patent number
US08669375B2

Reaction notes

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