Sodium Hydroxide → 3-Benzyloxy-5-methoxy-4-nitrophenol

HRID 1372603Notes

Reaction equation

HRID 1372603 reaction equation
[OH-:1].[Na+].F[C:4]1[CH:5]=[C:6]([O:21][CH3:22])[C:7]([N+:18]([O-:20])=[O:19])=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=1>CS(C)=O.Cl>[CH2:11]([O:10][C:8]1[CH:9]=[C:4]([OH:1])[CH:5]=[C:6]([O:21][CH3:22])[C:7]=1[N+:18]([O-:20])=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18433397Benzyl 5-fluoro-3-methoxy-2-nitrophenyl ether

Product 1

HCID 184333963-Benzyloxy-5-methoxy-4-nitrophenolYield 27%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

In 10N NaOH (5.8 ml, 58.0 mmol) and DMSO (20 ml), benzyl 5-fluoro-3-methoxy-2-nitrophenyl ether (5.35 g, 19.3 mmol) was stirred for 15 hours. The reaction mixture was poured in 1N HCl (100 ml), followed by extraction with ether (300 ml). The extract was washed with saturated brine (2×100 ml), dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from chloroform-ethyl acetate (4:1) eluate fractions, the title compound (1.43 g, 27%) was obtained as a brown oil.

Workup

  1. extractionfollowed by extraction with ether (300 ml)
  2. washThe extract was washed with saturated brine (2×100 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by chromatography on a silica gel column, whereby from chloroform-ethyl acetate (4:1) eluate fractions

Sources & evidence

ORD record
ord-097647f2c5894a538ec90925fc3ec1a8
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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