Diethyl Oxalate → 2-Oxo-4-phenylvaleric acid ethyl ester

HRID 1266428Notes

Reaction equation

HRID 1266428 reaction equation
C(O[C:4](=[O:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6])C.[Mg].[C:12]1([CH:18]([CH3:21])[CH2:19]Cl)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>C(OCC)C>[CH2:8]([O:7][C:5](=[O:6])[C:4](=[O:10])[CH2:19][CH:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:21])[CH3:9]

Participants

6

Reactant 4

HCID 7268Diethyl OxalateHCID 25517Ammonium ChlorideHCID 522778Cumene, beta-chloro-HCID 5462224Magnesium

Product 1

HCID 179356372-Oxo-4-phenylvaleric acid ethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A Grignard solution, to which 15 ml of oxalic acid diethyl ester is added at −30° C. within 30 minutes, is prepared from 2.6 g of magnesium chips and 15 ml of 2-phenyl-1-chloropropane in diethyl ether. It is stirred for one hour at −20° C. and for 2 hours at 0° C., and then mixed with saturated ammonium chloride solution. The diethyl ether phase is separated, dried (Na2SO4) and concentrated by evaporation and distilled in a vacuum. 17.7 g of 2-oxo-4-phenylvaleric acid ethyl ester, boiling point 98-100° C./0.03 hPa, is obtained.

Workup

  1. customThe diethyl ether phase is separated
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated by evaporation
  4. distillationdistilled in a vacuum

Sources & evidence

ORD record
ord-a36916d10a91470cbdd40b9a82ae497a
Source dataset
uspto-grants-2003_04
Patent number
US06548534B2

Reaction notes

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