Diethyl Oxalate → ETHYL 2-METHYLBENZOYLFORMATE

HRID 1954473Notes

Reaction equation

HRID 1954473 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.[C:11]1([CH3:19])[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Mg]Cl.[Cl-].[NH4+].CCCCCC.C(OCC)(=O)C>C1COCC1>[CH3:19][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:2]([C:1]([O:8][CH2:9][CH3:10])=[O:7])=[O:4]

Participants

6

Reactant 4

HCID 7268Diethyl OxalateHCID 25517Ammonium ChlorideHCID 21226206Ethyl acetate hexaneHCID 178424304HCID 178424304, compound

Product 1

HCID 11622483ETHYL 2-METHYLBENZOYLFORMATEYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

A solution of diethyl oxalate (30 g) in anhydrous THF (300 ml) was cooled to -30° C. A solution of o-tolyl magnesium chloride in THF (1 M, 140 ml) was added to the above solution at a temperature of the reaction solution of -20° C. After stirring at -30° C. for 30 minutes, the mixture was allowed to warm up to 0° C. and combined with an aqueous ammonium chloride solution. The mixture was concentrated under reduced pressure. The residue was treated with water and diethyl ether and phases were separated. The organic phase was washed with water, dried over anhydrous magnesium sulfate and concentrated to give a yellow oil. The oil was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=10/1) to give the desired ethyl 2-methylbenzoylformate (18 g, yield: 87%).

Workup

  1. temperatureto warm up to 0° C.
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionThe residue was treated with water and diethyl ether and phases
  4. customwere separated
  5. washThe organic phase was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto give a yellow oil

Sources & evidence

ORD record
ord-bfbfc1da1f074ca59cd62d54dd676d1a
Source dataset
uspto-grants-2000_09
Patent number
US06121476

Reaction notes

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