Hydrochloric Acid → HCID 57667922, compound

HRID 1673353Notes

Reaction equation

HRID 1673353 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([N+:19]([O-:21])=[O:20])[CH:10]=1.[C:22]1([OH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl>C(OCC)(=O)C.CN(C)C=O>[N+:19]([C:11]1[CH:10]=[C:9]([CH2:8][O:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14])([O-:21])=[O:20]

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

0.50 g of potassium carbonate and 0.50 g of methyl 4-(bromomethyl)-2-nitrobenzoate were added to 5 mL of N,N-dimethylformamide solution containing 0.18 g of phenol at room temperature and stirred at the 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 dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=6:1] to obtain 0.53 g of methyl 2-nitro-4-(phenoxymethyl)benzoate as colorless oil.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. washafter washed with a saturated sodium chloride aqueous solution
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=6:1]

Sources & evidence

ORD record
ord-d5c9aa073e774904aab0426ef7524663
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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