Hydrochloric Acid → HCID 57667922, compound

HRID 2191627Notes

Reaction equation

HRID 2191627 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([N+:26]([O-:28])=[O:27])[CH:17]=1.Cl>C(OCC)(=O)C.CN(C)C=O>[N+:26]([C:18]1[CH:17]=[C:16]([CH2:15][O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:25]=[CH:24][C:19]=1[C:20]([O:22][CH3:23])=[O:21])([O-:28])=[O:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 11430Potassium CarbonateHCID 19777981HCID 19777981, compound

Product 1

HCID 57667922HCID 57667922, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To N,N-dimethylformamide 5.0 mL solution of phenol 0.18 g were added potassium carbonate 0.50 g and methyl 4-(bromomethyl)-2-nitrobenzoate 0.50 g at room temperature, and it was stirred at same temperature for 10 hours. Ethyl acetate and 1.0 mol/L hydrochloric acid were added to the reaction mixture. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate=6:1] to give methyl 2-nitro-4-(phenoxymethyl)benzoate 0.53 g of colorless oil.

Workup

  1. customThe organic layer was separated
  2. washafter washing with saturated sodium chloride aqueous solution
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-387b7622aac64f568e5c984a38f71bfe
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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