Lithium Hydroxide → 4-((Methyl(phenyl)amino)methyl)benzoic acid

HRID 1501032Notes

Reaction equation

HRID 1501032 reaction equation
[CH3:1][N:2]([CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Li+]>O1CCCC1.CO.O>[CH3:1][N:2]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[CH:18][CH:19]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 28829589Methyl 4-{[methyl(phenyl)amino]methyl}benzoate

Product 1

HCID 167745434-((Methyl(phenyl)amino)methyl)benzoic acidYield 53%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-((methyl(phenyl)amino)methyl)benzoate (400 mg, 1.57 mmol) in tetrahydrofuran (30 mL) and methanol (10 mL) was added lithium hydroxide (210 mg, 5 mmol) in water (10 mL). The mixture was stirred at room temperature for 2 hours. The suspension was concentrated in vacuo and acidified with concentrated hydrochloric acid (12 N, 5 mL). The mixture was re-dissolved by water (50 mL) and dichloromethane (50 mL). Organic phase was separated and concentrated to give the product 4-((methyl(phenyl)amino)methyl)benzoic acid (200 mg, 53%) as a white solid.

Workup

  1. concentrationThe suspension was concentrated in vacuo
  2. dissolutionThe mixture was re-dissolved by water (50 mL) and dichloromethane (50 mL)
  3. customOrganic phase was separated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e37b57fc2db64b7a912b772ee7bf4ef3
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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