Toluene → HCID 69714704, compound

HRID 495347Notes

Reaction equation

HRID 495347 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.C([O-])(O)=O.[Na+].[C:16]1(C)C=CC=C[CH:17]=1>N1C=CC=CC=1>[CH2:8]([CH:9]1[CH2:10][CH2:5][CH:3]=[CH:2][O:1]1)[CH2:7][CH:6]=[CH:16][CH3:17]

Participants

5

Reactant 3

HCID 1140TolueneHCID 68490alpha-HydroxyacetophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 69714704HCID 69714704, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

The acetyl derivative derived from the fragrant lactone (5 mmol) and pyridine (3-4 drops, 0.1 eq.) was added to a suspension of the hydroxy-acetophenone (10 mmol) in toluene (10 ml) The mixture was heated under reflux overnight. It was then poured into aq. NaHCO3 (sat.) and the separated aqueous phase was extracted with MTBE. The combined organic layers were washed with brine and dried over MgSO4. The crude, obtained after evaporation of the solvents, was purified by chromatography (SiO2, EtOAc/Hexane) to afford the desired product as a colorless to pale yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. extractionthe separated aqueous phase was extracted with MTBE
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customThe crude, obtained
  7. customafter evaporation of the solvents
  8. customwas purified by chromatography (SiO2, EtOAc/Hexane)

Sources & evidence

ORD record
ord-c211f1c8068042da8092d62f6337ad00
Source dataset
uspto-grants-2005_09
Patent number
US06939845B2

Reaction notes

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