Sodium Hydroxide → 5-(Benzyloxy)-4-methoxy-2-nitrobenzoic acid

HRID 1406991Notes

Reaction equation

HRID 1406991 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([O:28][CH3:29])=[CH:11][C:12]([N+:25]([O-:27])=[O:26])=[C:13]([CH:24]=1)[C:14]([O:16]CC1C=CC=CC=1)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CCO.O>[CH2:1]([O:8][C:9]1[C:10]([O:28][CH3:29])=[CH:11][C:12]([N+:25]([O-:27])=[O:26])=[C:13]([CH:24]=1)[C:14]([OH:16])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 59362000Benzyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate

Product 1

HCID 8212205-(Benzyloxy)-4-methoxy-2-nitrobenzoic acidYield 94.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of benzyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate (1.4 g, 3.56 mmol) in EtOH (10 mL) was added 1N NaOH (4.27 mL, 4.27 mmol). The mixture was stirred at RT for 1 h, upon which an additional aliquot of NaOH (4.27 mL, 4.27 mmol) was added. Stirring was continued at RT overnight. The mixture was diluted with water (20 mL) and washed with CH2Cl2 (2×25 mL). The aqueous layer was acidified to pH=2 with 0.5 N HCl and extracted with EtOAc (3×50 mL). The combined organics were dried (Na2SO4), filtered and concentrated in vacuo to give 5-(benzyloxy)-4-methoxy-2-nitrobenzoic acid (1.02 g, 3.37 mmol, 94%).

Workup

  1. additionwas added
  2. washwashed with CH2Cl2 (2×25 mL)
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-671cba4a46f94d59b31cfe80a7a31a1c
Source dataset
uspto-grants-2014_12
Patent number
US08916576B2

Reaction notes

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