2-Chlorobenzaldehyde → 2',5-Dichloro-2-methylaminobenzhydrol

Participants

Reaction Steps

To a solution of boron trichloride (100 mg) in dry benzene (5 ml), a solution of p-chloromethylaniline (100 mg) in dry benzene (2 ml) is added with cold water cooling (7°-10° C.), and the resultant mixture is refluxed for 2 hours. Then, a solution of o-chlorobenzaldehyde (99 mg) and tri-n-butylamine (131 mg) in dry benzene (2 ml) is added thereto with cold water cooling, and the mixture is stirred at room temperature for 1 hour. The reaction mixture is mixed with ice pieces and shaken with ether. The ethereal layer is washed with aqueous sodium carbonate and a saturated brine in that order, dried over potassium carbonate, and evaporated under reduced pressure. The residue is chromatographed on a column of silica gel, and the product is recrystallized from chloroform-petroleum ether to give 2-methylamino-5,2'-dichlorobenzhydrol (174 mg) as crystals melting at 106° to 108° C. The yield is 87.4%.

Provenance & Evidence