Lithium Hydroxide → 4-(2-Dimethylamino-ethoxy)-benzoic acid

HRID 499189Notes

Reaction equation

HRID 499189 reaction equation
C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])=[CH:6][CH:5]=1.[OH-].[Li+]>CO>[CH3:14][N:13]([CH3:15])[CH2:12][CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:16])=[O:2])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 14638321Methyl 4-(2-(dimethylamino)ethoxy)benzoate

Product 1

HCID 64866194-(2-Dimethylamino-ethoxy)-benzoic acidYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 4-[2-(dimethylamino)-ethoxy]-benzoic acid methyl ester (3 mmol) in methanol (10 mL) is added a lithium hydroxide solution (2 M, 20 mL). The reaction mixture is stirred at 22° C. for 15 min. After removal of the solvent, the residue is re-dissolved in methanol, passed through a SCX column, washed with methanol, and eluded with 2M ammonia in methanol. After solvent is evaporated, a white solid is obtained (500 mg, 80% yield, ES−(m/z) 208.2 [M−H]).

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe residue is re-dissolved in methanol
  3. washwashed with methanol
  4. customAfter solvent is evaporated
  5. customa white solid is obtained (500 mg, 80% yield, ES−(m/z) 208.2 [M−H])

Sources & evidence

ORD record
ord-e1c67b8f055b4298b1fe2e7b2e17c642
Source dataset
uspto-grants-2010_08
Patent number
US07767674B2

Reaction notes

Loading…