Sulfuric Acid → Diethyl 2-methyl-3,4,6-trifluorobenzoylmalonate

HRID 864330

Reaction equation

HRID 864330 reaction equation
[Mg].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:13][C:14]1[C:22]([F:23])=[C:21]([F:24])[CH:20]=[C:19]([F:25])[C:15]=1[C:16](Cl)=[O:17].S(=O)(=O)(O)O>C(Cl)(Cl)(Cl)Cl.C(O)C.C1(C)C=CC=CC=1.O>[CH3:13][C:14]1[C:22]([F:23])=[C:21]([F:24])[CH:20]=[C:19]([F:25])[C:15]=1[C:16]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])=[O:17]

Participants

9

Reactant 4

HCID 1118Sulfuric AcidHCID 7761Diethyl MalonateHCID 5462224MagnesiumHCID 150076072-Methyl-3,4,6-trifluorobenzoyl chloride

Product 1

HCID 17879412Diethyl 2-methyl-3,4,6-trifluorobenzoylmalonate

Reagents, catalysts & solvents 4

HCID 5943Carbon TetrachlorideCatalystHCID 702EthanolSolvent2×HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

Separately, two drops of carbon tetrachloride are added to a solution of metallic magnesium (0.4 g) in absolute ethanol (0.9 ml). When the reaction starts, a mixture of diethyl malonate (2.6 ml), absolute ethanol (1.6 ml) and anhydrous toluene (6 ml) is added dropwise below 60° C. After stirring at 60° C. for 1 hour, the reaction mixture is cooled to 0° C. and thereto a solution of 2-methyl-3,4,6-trifluorobenzoyl chloride prepared above in toluene (5 ml) is added dropwise. After stirring for 30 minutes, a mixture of conc. sulfuric acid (0.4 ml) and water (6 ml) is added and the mixture is extracted with diethyl ether, and the extract is dried over magnesium sulfate and concentrated to give diethyl 2-methyl-3,4,6-trifluorobenzoylmalonate (5.2 g).

Workup

  1. additionis added dropwise below 60° C
  2. temperaturethe reaction mixture is cooled to 0° C.
  3. additionis added dropwise
  4. stirringAfter stirring for 30 minutes
  5. additionis added
  6. extractionthe mixture is extracted with diethyl ether
  7. dry with materialthe extract is dried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9caa029acfe1496d9f01e34ec6b97123
Source dataset
uspto-grants-1996_10
Patent number
US05563138

Linked notes

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