Hydrochloric Acid → Ethyl 2-oxo-3-phenylpropanoate

HRID 430641Notes

Reaction equation

HRID 430641 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.[CH2:11]([Mg]Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>C(OCC)C>[O:4]=[C:2]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:1]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 178418336HCID 178418336, compound

Product 1

HCID 12292599Ethyl 2-oxo-3-phenylpropanoateYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-60 °C

Procedure

A solution of diethyl oxalate (11.15 mL, 82.1 mmol) in diethyl ether (50 mL) at −78° C. was treated dropwise with 1 M benzylmagnesium chloride in diethyl ether (82 mL, 82 mmol) while maintaining an internal temperature of −60° C. The mixture was stirred for 30 minutes and poured into a mixture of concentrated HCl (8 mL), ice (40 mL), and diethyl ether (50 mL). The organic phase was washed with water and brine, dried (MgSO4), filtered, and concentrated to provide 15.5 g (98%) of the desired product of sufficient purity for subsequent use.

Workup

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cdaa373e3812485f97b896f848dab473
Source dataset
uspto-grants-2001_11
Patent number
US06323228B1

Reaction notes

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