Potassium Carbonate → HCID 22258876, compound

HRID 1611124Notes

Reaction equation

HRID 1611124 reaction equation
[OH:1][CH:2]([C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:13])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>CC(C)=O>[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][O:13][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:4]=2[CH:2]([OH:1])[CH3:3])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 222589412-Hydroxy-α-methyl-6-nitrobenzenemethanol

Product 1

HCID 22258876HCID 22258876, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 2-(1-hydroxyethyl)-3-nitrophenol (0.300 g, 1.638 mmol) in acetone (5 mL) was added potassium carbonate (0.25 g, 1.802 mmol). The mixture was stirred at room temperature for 15 min, and 4-methoxybenzyl chloride (0.22 mL, 1.638 mmol) was added to the mixture. The mixture was stirred at room temperature for 2 hrs and at 60° C. for 3 hrs. The reaction was quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=4/1). The purified compound was washed with diisopropyl ether to give 1-{2-[(4-methoxybenzyl)oxy]-6-nitrophenyl}ethanol as a white solid (0.201 g, yield; 41%).

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hrs and at 60° C. for 3 hrs
  2. customThe reaction was quenched with saturated aqueous ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=4/1)
  8. washThe purified compound was washed with diisopropyl ether

Sources & evidence

ORD record
ord-7544ef23afdb4c659b7229e47ae25d2a
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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