Sulfuric Acid → Ethyl 2-(1,3,5-triethylphenyl)-2-oxoacetate

HRID 579244Notes

Reaction equation

HRID 579244 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.[CH2:11]([C:13]1([Mg]Br)[CH:18]=[C:17]([CH2:19][CH3:20])[CH:16]=[C:15]([CH2:21][CH3:22])[CH2:14]1)[CH3:12].S(=O)(=O)(O)O>O1CCCC1>[CH2:19]([C:17]1([C:2](=[O:4])[C:1]([O:8][CH2:9][CH3:10])=[O:7])[CH:18]=[C:13]([CH2:11][CH3:12])[CH:14]=[C:15]([CH2:21][CH3:22])[CH2:16]1)[CH3:20]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7268Diethyl OxalateHCID 178436339HCID 178436339, compound

Product 1

HCID 66691385Ethyl 2-(1,3,5-triethylphenyl)-2-oxoacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

On the other hand, to a 3 L volume four-necked flask, diethyl oxalate (295 g) and tetrahydrofuran (anhydrous) (350 ml) were added under a nitrogen atmosphere and cooled on ice-bath. The above mentioned solution of 1,3,5-triethylphenylmagnesium bromide in tetrahydrofuran was added thereto with keeping the temperature below 10° C. The resulting mixture was stirred at room temperature for 2 hours. The pH of the mixture was adjusted to less than 2 with 20 w/w % of sulfuric acid under ice-cooling. The mixture was extracted with toluene. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 495.3 g of ethyl 2-(1,3,5-triethylphenyl)-2-oxoacetate (9-b).

Workup

  1. temperaturecooled on ice-bath
  2. additionwas added
  3. customthe temperature below 10° C
  4. temperaturecooling
  5. extractionThe mixture was extracted with toluene
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cd290c5279654a0b87358327b327b6d4
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

Loading…