Ethanol → Ethyl p-tolylacetate

HRID 1184947Notes

Reaction equation

HRID 1184947 reaction equation
[CH2:1](O)[CH3:2].[C:4]1([CH3:14])[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:4]1([CH3:14])[CH:5]=[CH:6][C:7]([CH2:10][C:11]([O:13][CH2:1][CH3:2])=[O:12])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 248474p-Tolylacetic acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 84175Ethyl p-tolylacetateYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Toluene (100 ml), ethanol (9.20 g, 199.77 mmol) and p-tolylacetic acid (25 g, 166.48 mmol) was added into a 200-ml flask in this order at room temperature and then p-toluenesulfonic acid monohydrate (4.75 g, 24.97 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 (4.21 g, 41.62 mmol) at room temperature, stirred and then added with silica gel. After stirring for a while, the silica gel was filtered off. After the solvent of the filtrate was removed in vacuum distillation, ethyl p-tolylacetate (28.09 g, 95%) 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. stirringAfter stirring 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-69946d6464684fdda6507e33cd97d02a
Source dataset
uspto-grants-2014_03
Patent number
US08669375B2

Reaction notes

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