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

HRID 1461426Notes

Reaction equation

HRID 1461426 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-bf6f1560281b4c3fb56b9f266e499b43
Source dataset
uspto-grants-1991_12
Patent number
US05075330

Reaction notes

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