Reaction #302884

Reaction equation

diethyl oxalate

toluene

sulfuric acid

→

ethyl 2-(methyl-phenyl)-2-oxoacetate

Yield 30.3%

Conditions

Workup

1. 1
   workup.ADDITIONabove was added dropwise at −40° C.
2. 2
   Otheran organic layer was recovered
3. 3
   WashThe resulting organic layer was washed with 134 g of water
4. 4
   Dryingdried with magnesium sulfate
5. 5
   ConcentrationAfter concentration
6. 6
   Otherwith an evaporator, distillation
7. 7
   Otherunder high vacuum, and silica gel column purification

Procedure

A solution of 83 g of diethyl oxalate in toluene (170 g) was cooled to −40° C. or lower. The Grignard reagent prepared as described above was added dropwise at −40° C. or lower, and this was retained at −40° C. for 2 hours. To the reaction mixture was added 234 g of 10% sulfuric acid, and an organic layer was recovered. The resulting organic layer was washed with 134 g of water, and dried with magnesium sulfate. After concentration with an evaporator, distillation under high vacuum, and silica gel column purification afforded 33.1 g of ethyl 2-(methyl-phenyl)-2-oxoacetate.

Source