Sodium Hydroxide → HCID 86615989, compound

HRID 1914337Notes

Reaction equation

HRID 1914337 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([O:16][C:17]2[CH:18]=[N:19][C:20]([Cl:24])=[C:21]([CH3:23])[CH:22]=2)[CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[Cl:24][C:20]1[N:19]=[CH:18][C:17]([O:16][CH:10]([C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:25])=[O:2])=[CH:9][CH:8]=2)[CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[CH:22][C:21]=1[CH3:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86615988HCID 86615988, compound

Product 1

HCID 86615989HCID 86615989, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 4-[1-(6-chloro-5-methyl-pyridin-3-yloxy)-3,3-dimethyl-butyl]-benzoic acid methyl ester (440 mg) in methanol (30 mL) is added sodium hydroxide (5 N aqueous, 2 mL) and stirred for 5 h. The reaction mixture is concentrated and acidified by 5 N HCl (2 mL), extracted with ethyl acetate. Combined organic layers are washed with water and brine, dried over sodium sulfate. Concentration gives the titled compound (414 mg).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. extractionextracted with ethyl acetate
  3. washCombined organic layers are washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration

Sources & evidence

ORD record
ord-834081d9cd194887a3ee599dbf50bf35
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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