Hydrochloric Acid → Ethyl 2-(4-methylphenyl)-2-oxoacetate

HRID 2269805Notes

Reaction equation

HRID 2269805 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([Mg]Br)=[CH:3][CH:2]=1.[C:10](OCC)(=[O:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl>CCOCC.O1CCCC1>[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([C:10](=[O:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 178418370HCID 178418370, compound

Product 1

HCID 2736443Ethyl 2-(4-methylphenyl)-2-oxoacetateYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 1.0 M solution of 4-tolylmagnesium bromide in ether (20.5 ml) is added dropwise to a solution of diethyl oxalate (6.5 g) in anhydrous tetrahydrofuran (41 ml) under a nitrogen atmosphere and ice cooling. Five minutes after completing the addition, the mixture is stirred at room temperature for 1.5 hours. To the reaction mixture is added 1 N hydrochloric acid, and the whole is extracted with ether. The organic layer is washed with water and saturated brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography to give 2.99 g (76%) of ethyl 4-tolylglyoxylate.

Workup

  1. customFive minutes
  2. additionthe addition
  3. extractionthe whole is extracted with ether
  4. washThe organic layer is washed with water and saturated brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-aae11e2ee4114aa6baa462962792efb2
Source dataset
uspto-grants-2001_12
Patent number
US06329547B1

Reaction notes

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