Ethanol → 4-Ethylresorcinol

HRID 1072950Notes

Reaction equation

HRID 1072950 reaction equation
C(O)C.[CH3:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]([OH:14])=[CH:11][C:12]=1[OH:13])=O>O>[CH2:5]([C:7]1[CH:8]=[CH:9][C:10]([OH:14])=[CH:11][C:12]=1[OH:13])[CH3:4]

Participants

4

Reactant 2

HCID 702Ethanol2×HCID 69902',4'-Dihydroxyacetophenone

Product 1

HCID 179274-Ethylresorcinol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In a three necked round bottom flask (equipped with a condenser, additional funnel and mechanical stirrer) was added the catalyst or combination of the catalysts. 100 ml of a mixture of 50:50 ethanol:water was added and the reaction was heated to reflux conditions. 2,4-dihydroxy acetophenone in 100 ml of water:ethanol mixture with or without acids was placed in the additional funnel and was added to the mixture (dropwise-2-4 hrs). The reaction was filtered through a milipore filter and concentrated in vacuo to give a solid. This solid was crystalized from 1,2-dichloroethane to give 4-ethyl resorcinol. The unreacted 2,4-dihydroxy acetophenone is recovered from the media and recycled. The structure of 4-ethyl resorcinol and 2,4-dihydroxy acetophenone were characterized by NMR, Gas Chromatography, IR and Mass spectroscopy

Workup

  1. customIn a three necked round bottom flask (equipped with a condenser, additional funnel and mechanical stirrer)
  2. additionwas added the catalyst or combination of the catalysts
  3. temperaturethe reaction was heated
  4. temperatureto reflux conditions
  5. additionwas added to the mixture (dropwise-2-4 hrs)
  6. filtrationThe reaction was filtered through a milipore
  7. filtrationfilter
  8. concentrationconcentrated in vacuo
  9. customto give a solid
  10. customThis solid was crystalized from 1,2-dichloroethane

Sources & evidence

ORD record
ord-65a1d4c8cfdc4ccc8fd7ebb5cd2fafac
Source dataset
uspto-grants-2005_06
Patent number
US06911562B2

Reaction notes

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