Methanol → 2,4-Dichloro-3-[2-(1H-tetrazol-1-yl)ethoxy]benzoic acid

HRID 659933Notes

Reaction equation

HRID 659933 reaction equation
CO.[Cl:3][C:4]1[C:14]([O:15][CH2:16][CH2:17][N:18]2[CH:22]=[N:21][N:20]=[N:19]2)=[C:13]([Cl:23])[CH:12]=[CH:11][C:5]=1[C:6]([O:8]CC)=[O:7].[OH-].[Na+]>O>[Cl:3][C:4]1[C:14]([O:15][CH2:16][CH2:17][N:18]2[CH:22]=[N:21][N:20]=[N:19]2)=[C:13]([Cl:23])[CH:12]=[CH:11][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 57437285ethyl 2,4-dichloro-3-[2-(1H-tetrazol-1-yl)ethoxy]benzoate

Product 1

HCID 574372702,4-Dichloro-3-[2-(1H-tetrazol-1-yl)ethoxy]benzoic acidYield 85.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a methanol (15 ml) solution of ethyl 2,4-dichloro-3-[2-(1H-tetrazol-1-yl)ethoxy]benzoate (0.88 g) were added sodium hydroxide (0.16 g) and water (5 ml), and the mixture was stirred at room temperature for 7 hours. After the addition of water (20 ml) and concentration at reduced pressure, an aqueous sodium hydroxide solution was added and the mixture was washed with ethyl acetate (50 ml). The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off to obtain the desired 2,4-dichloro-3-[2-(1H-tetrazol-1-yl)ethyloxy]-benzoic acid (0.69 g).

Workup

  1. washthe mixture was washed with ethyl acetate (50 ml)
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationEthyl acetate was distilled off

Sources & evidence

ORD record
ord-104bb2c3b6624ea28e6352b3d5e9c5a9
Source dataset
uspto-grants-2011_12
Patent number
US08084398B2

Reaction notes

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