Nitric Acid → HCID 21958891, compound

HRID 2233243Notes

Reaction equation

HRID 2233243 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[F:10][C:11]([F:28])([F:27])[CH2:12][O:13][C:14]1[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][C:15]=1[O:25][CH3:26]>ClCCl.C(O)(=O)C.O>[CH3:26][O:25][C:15]1[CH:16]=[C:17]([C:23]([N+:6]([O-:9])=[O:7])=[CH:24][C:14]=1[O:13][CH2:12][C:11]([F:10])([F:28])[F:27])[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

7

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 21958895HCID 21958895, compound

Product 1

HCID 21958891HCID 21958891, compoundYield 52.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Concentrated sulphuric acid (64 ml) and concentrated nitric acid (10.0 ml, 0.152 mol) were added cautiously, over 1 hour, to a two-phase system containing a stirred solution of ethyl 4-(2,2,2-trifluoroethoxy)-3-methoxybenzoate (35.3 g, 0.127 mol) in dichloromethane (340 ml), acetic acid (173 ml) and water (40 ml) at 5° C. The reaction was allowed to warm to ambient temperature over 60 hours (with vigorous mechanical stirring), the aqueous phase was separated, and the organic phase washed with water (6×250 ml). The organic phase was concentrated to a total volume of ˜200 ml, isohexane (150 ml) was added and the solid which precipitated out was collected by suction filtration. Drying of the solid in vacuo yielded ethyl 3-methoxy-4-(2,2,2-trifluoroethoxy)-6-nitrobenzoate (21.7 g, 52% yield) as a yellow solid. The mother liquors contained a mixture of product (28%) and starting material (72%) which was recycled in a latter reaction:

Workup

  1. customthe aqueous phase was separated
  2. washthe organic phase washed with water (6×250 ml)
  3. concentrationThe organic phase was concentrated to a total volume of ˜200 ml, isohexane (150 ml)
  4. additionwas added
  5. customthe solid which precipitated out
  6. filtrationwas collected by suction filtration
  7. customDrying of the solid in vacuo

Sources & evidence

ORD record
ord-67c063e0cbe843efbe40c59124c6efa6
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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