Hydrochloric Acid → Methyl (2-methylphenyl)(oxo)acetate

HRID 1278976Notes

Reaction equation

HRID 1278976 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:9].[C:10]([O:16][CH3:17])(=[O:15])[C:11](OC)=[O:12].Cl>CCOCC.CCCCCC.C(OCC)(=O)C>[CH3:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:11]([C:10]([O:16][CH3:17])=[O:15])=[O:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 72362-BromotolueneHCID 11120Dimethyl oxalateHCID 5462224Magnesium

Product 1

HCID 3768392Methyl (2-methylphenyl)(oxo)acetateYield 68%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.1 g of magnesium (0.21 mol) was placed in 300 ml of dry ether and 34.18 g of o-bromotoluene (0.2 mol) was added dropwise thereto under a nitrogen atmosphere to prepare a Grignard reagent. The Grignard reagent solution was cooled to −78° C. and 23.6 g of dimethyl oxalate (0.2 mol) was added dropwise thereto. The resulting solution was stirred for 30 minutes, mixed with crushed ice, acidified with 20% hydrochloric acid and then extracted with ether. The organic layer was washed three times with water, dried over magnesium sulfate, and the solvent was removed under a reduced pressure to obtain a residue. The residue was subjected to column chromatography using a mixture of n-hexane and ethyl acetate (9:1) as an eluent to obtain 24.2 g (yield 68%) of the title compound as a colorless liquid.

Workup

  1. additionmixed with crushed ice
  2. extractionextracted with ether
  3. washThe organic layer was washed three times with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was removed under a reduced pressure
  6. customto obtain a residue

Sources & evidence

ORD record
ord-c4a023edb87641c4a3e3060dd714102a
Source dataset
uspto-grants-2002_09
Patent number
US06444850B1

Reaction notes

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