Sulfuric Acid → ETHYL 2-METHYLBENZOYLFORMATE

HRID 888710Notes

Reaction equation

HRID 888710 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.S(=O)(=O)(O)O.[C:16]1([CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH3:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:2](=[O:4])[C:1]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 7268Diethyl Oxalate

Product 1

HCID 11622483ETHYL 2-METHYLBENZOYLFORMATEYield 30.3%

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.

Workup

  1. additionabove was added dropwise at −40° C.
  2. customan organic layer was recovered
  3. washThe resulting organic layer was washed with 134 g of water
  4. dry with materialdried with magnesium sulfate
  5. concentrationAfter concentration
  6. customwith an evaporator, distillation
  7. customunder high vacuum, and silica gel column purification

Sources & evidence

ORD record
ord-1deec8ef53894b4d99277a62db4497fc
Source dataset
uspto-grants-2012_08
Patent number
US08252563B2

Reaction notes

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