2-[(2,3-Dimethylphenyl)amino]benzenemethanol → HCID 15027376, compound

HRID 703209Notes

Reaction equation

HRID 703209 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[NH:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][OH:24]>ClCCl>[CH3:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[NH:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=[O:24]

Participants

4

Reactant 2

HCID 150273742-[(2,3-Dimethylphenyl)amino]benzenemethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 15027376HCID 15027376, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of pyridinium chlorochromate (47.5 g, 0.22 mol) and neutral alumina (170 g) in dichloromethane (600 ml) is stirred for 30 minutes at room temperature. 2-[(2,3-dimethylphenyl)amino]benzyl alcohol (25 g, 0.11 mol) is added and the reaction mixture is stirred at room temperature overnight. The suspension is filtered through a pad of silica gel (1000 g) and the product is eluted with dichloromethane (2500 ml). The combined filtrate and eluant are evaporated and the residue is recrystallized from cold methanol/water to give 2-[(2,3-dimethylphenyl)amino]benzaldehyde (11.95 g, 48%). Recrystallization from hexane at 0° C. gives analytical material; mp 45°-47° C.

Workup

  1. stirringthe reaction mixture is stirred at room temperature overnight
  2. filtrationThe suspension is filtered through a pad of silica gel (1000 g)
  3. washthe product is eluted with dichloromethane (2500 ml)
  4. customThe combined filtrate and eluant are evaporated
  5. customthe residue is recrystallized from cold methanol/water

Sources & evidence

ORD record
ord-cf3dae5597544055be96e2d4003bb016
Source dataset
uspto-grants-1991_01
Patent number
US04981865

Reaction notes

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