Sulfuric Acid → HCID 53848590, compound

HRID 1607678Notes

Reaction equation

HRID 1607678 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Mg].[F:13][C:14]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:15]=1[O:16][C:17]1[C:18]([N+:27]([O-:29])=[O:28])=[CH:19][C:20]([CH3:26])=[C:21]([CH:25]=1)[C:22](Cl)=[O:23].S(=O)(=O)(O)O>CCOCC.C(Cl)(Cl)(Cl)Cl.C(O)C>[F:13][C:14]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:15]=1[O:16][C:17]1[C:18]([N+:27]([O-:29])=[O:28])=[CH:19][C:20]([CH3:26])=[C:21]([CH:25]=1)[C:22]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[O:23]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 7761Diethyl MalonateHCID 5462224MagnesiumHCID 11723984HCID 11723984, compound

Product 1

HCID 53848590HCID 53848590, compoundYield 95.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent3×HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-(2,4-difluorophenoxy)-2-methyl-4-nitrobenzoic acid (1.4 g) and phosphorus pentachloride (1 g) in benzene (10 ml) was stirred for 1 hour at room temperature. The mixture was concentrated under reduced pressure to give an oil of 5-(2,4-difluorophenoxy)-2-methyl-4-nitrobenzoyl chloride (1.6 g). A solution of diethyl malonate (0.88 g) and ethanol (0.5 ml) in ether (5 ml) was added dropwise to a stirred solution of magnesium (132 mg), ethanol (0.2 ml), and carbon tetrachloride (0.3 ml) in ether (5 ml) at room temperature. The mixture was stirred for 1 hour at room temperature and refluxed for 30 minutes. To the resulting mixture was added dropwise a solution of 5-(2,4-difluorophenoxy)-2-methyl-4-nitrobenzoyl chloride (1.6 g) in ether (3 ml) at 5° C. The mixture was stirred for 2 hours at room temperature and refluxed for 1 hour. The reaction mixture was poured into 10% sulfuric acid (40 ml) and extracted with ethyl acetate. The extract was washed with water, dried, and concentrated to give an oil of diethyl 5-(2,4-difluorophenoxy)-2-methyl-4-nitrobenzoylmalonate (2.1 g).

Workup

  1. temperaturerefluxed for 30 minutes
  2. stirringThe mixture was stirred for 2 hours at room temperature
  3. temperaturerefluxed for 1 hour
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-07c807f3f51f478889e1d632902a9c71
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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