Methanol → HCID 66775223, compound

HRID 1644621Notes

Reaction equation

HRID 1644621 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=1)[C:9]([O:11]C)=[O:10].CO.[OH-].[Na+]>O>[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 59242991HCID 59242991, compound

Product 1

HCID 66775223HCID 66775223, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a clean, dry 100 mL round bottom flask is added methyl 3-(2-fluorobenzyloxy)-5-nitrobenzoate (0.49 g, 1.6 mmole, 1 eq), methanol (5 mL) and 1M sodium hydroxide in water (20 mL). The reaction mixture was stirred at room temperature for 18 h and then quenched with 1M HCl and ethyl acetate. The product was extracted into the organic layer, dried over magnesium sulfate, filtered and evaporated. A white solid was obtained (0.4 g, 85% yield). Calc'd for C14H10NFO5; m/z (M+H+)=292; found 292.

Workup

  1. customTo a clean, dry 100 mL round bottom flask
  2. customquenched with 1M HCl and ethyl acetate
  3. extractionThe product was extracted into the organic layer
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customA white solid was obtained (0.4 g, 85% yield)

Sources & evidence

ORD record
ord-406285289c4c4c14837979b28a7ff98c
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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