Tetrahydrofuran → 1-(3-Methoxy-2-methylphenyl)ethanone

HRID 1985900Notes

Reaction equation

HRID 1985900 reaction equation
[CH3:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.O1CCC[CH2:14]1.C[Mg]Br.[Cl-].[NH4+]>S(Cl)(Cl)=O.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Fe]>[CH3:12][O:11][C:10]1[C:2]([CH3:1])=[C:3]([C:4](=[O:6])[CH3:14])[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 70214833-Methoxy-2-MethylBenzoic AcidHCID 178418573HCID 178418573, compound

Product 1

HCID 197023421-(3-Methoxy-2-methylphenyl)ethanone

Reagents, catalysts & solvents 2

HCID 11110968Iron (III) acetylacetonateCatalystHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 2-methyl-3-methoxybenzoic acid (10.0 g, 60.2 mmol) in thionyl chloride (50 ml) was heated at reflux for 1 h and then cooled and concentrated in vacuo. To the residue was added tetrahydrofuran (100 ml) and iron (III) acetylacetonate (638 mg, 1.8 mmol) and the solution was cooled to −20° C., before addition of methylmagnesium bromide (3M in diethyl ether, 22.1 ml, 66.2 mmol). After stirring for 15 min, the mixture was poured into saturated aqueous ammonium chloride solution and extracted with dichloromethane. The combined extracts were washed with saturated aqueous sodium hydrogen carbonate solution, dried (MgSO4) and concentrated in vacuo.

Workup

  1. temperatureat reflux for 1 h
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. extractionextracted with dichloromethane
  5. washThe combined extracts were washed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-50598be9e4a84d07951ebf43dd0d8a74
Source dataset
uspto-grants-2009_06
Patent number
US07547718B2

Reaction notes

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