Benzoic acid, 2-((2,3-dimethylphenyl)amino)-, methyl ester → 2-[(2,3-Dimethylphenyl)amino]benzenemethanol

HRID 1195873Notes

Reaction equation

HRID 1195873 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[C:12](OC)=[O:13].[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[CH2:12][OH:13]

Participants

4

Reactant 2

HCID 71040Benzoic acid, 2-((2,3-dimethylphenyl)amino)-, methyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 150273742-[(2,3-Dimethylphenyl)amino]benzenemethanolYield 94.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-[(2,3-dimethylphenyl) amino]benzoic acid, methyl ester (31 g, 121.5 mmol) in dry ether (600 ml) is added dropwise to a suspension of lithium aluminum hydride (6.9 g, 0.18 mmol) in dry ether (200 ml) under an atmosphere of dry nitrogen. The reaction mixture is stirred at room temperature overnight and quenched by the careful dropwise addition of water (7 ml), 15% NaOH (7 ml) and water (20 ml). The resulting suspension is filtered and the filtrate is evaporated to an oil which crystallizes upon addition of hexane to give pure 2-[(2,3-dimethylphenyl)amino]benzyl alcohol (26 g, 94%); mp 65°-69° C.

Workup

  1. customquenched by the careful dropwise addition of water (7 ml), 15% NaOH (7 ml) and water (20 ml)
  2. filtrationThe resulting suspension is filtered
  3. customthe filtrate is evaporated to an oil which
  4. customcrystallizes upon addition of hexane

Sources & evidence

ORD record
ord-073499d8f7e34a348f7358873e932fb4
Source dataset
uspto-grants-1992_05
Patent number
US05112846

Reaction notes

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