Methanol → Methyl 4-benzoylbutyrate

HRID 1984798Notes

Reaction equation

HRID 1984798 reaction equation
[C:1]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15]O>S(=O)(=O)(O)O>[C:1]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 73914delta-Oxobenzenepentanoic acid

Product 1

HCID 137042Methyl 4-benzoylbutyrate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

Precursors suitable for preparation of fullerene derivatives were prepared. First, methyl 4-benzoylbutyrate was prepared as follows. A solution of 4-benzoylbutyric acid (11.9 g, 0.0619 mol) in MeOH (250 ml) with a catalytic amount of sulfuric acid (96%, 6 drops) was refluxed for 5 hours. Solvent was removed and 50 ml water was added. The reaction product was extracted with dichloromethane to provide an organic layer. The organic layer was separated, dried over MgSO4 and passed through a plug of silica, which was rinsed with 2% acetone in dichloromethane. Solvent was removed to afford the methyl ester as light-yellowish oil (12.57 g, 99%).

Workup

  1. customwere prepared
  2. customSolvent was removed
  3. addition50 ml water was added
  4. extractionThe reaction product was extracted with dichloromethane
  5. customto provide an organic layer
  6. customThe organic layer was separated
  7. dry with materialdried over MgSO4
  8. washwas rinsed with 2% acetone in dichloromethane
  9. customSolvent was removed

Sources & evidence

ORD record
ord-dfdc45aa7c4b4019b239f6a3887ab327
Source dataset
uspto-grants-2009_06
Patent number
US07544747B2

Reaction notes

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