Hydrochloric Acid → methyl 4-(2-chlorophenyl)-2,4-dioxobutanoate

HRID 1498930Notes

Reaction equation

HRID 1498930 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[C:11](OC)(=[O:16])[C:12]([O:14][CH3:15])=[O:13].[H-].[Na+].Cl>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH2:9][C:11](=[O:16])[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11120Dimethyl oxalateHCID 24758Sodium hydrideHCID 72864Ethanone, 1-(2-chlorophenyl)-

Product 1

HCID 2763945methyl 4-(2-chlorophenyl)-2,4-dioxobutanoateYield 69.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

In dimethylformamide (22 ml), 1-(2-chlorophenyl)ethanone (3.56 g) and dimethyl oxalate (3.26 g) were dissolved, and 60% sodium hydride suspension in oil (1.1 g) was added thereto while stirring at 5° C. The mixture was heated at a room temperature for one hour and then at 50° C. for 30 minutes. After being allowed to cool, the mixture was acidified with 2-N hydrochloric acid, and the precipitated crystal was separated by filtration, washed with water, and dried to give the title compound (3.83 g, 69%).

Workup

  1. temperatureThe mixture was heated at a room temperature for one hour
  2. temperatureto cool
  3. customthe precipitated crystal was separated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-fc3972b7539e4583a1e022f6a5781c0c
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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