Reaction #1563896

Reaction equation

2-isopropylaminophenylmethanol

→

2-isopropylaminobenzaldehyde

Yield 90.6%

Solvents

toluene

Conditions

Workup

1. 1
   Temperatureto cool to room temperature overnight
2. 2
   Filtrationfiltered through a pad of Celite which
3. 3
   Washwas eluted with toluene
4. 4
   ConcentrationThe filtrate was concentrated under reduced pressure

Procedure

Manganese dioxide (85% 182.6 g, 1.79 mol) was added to a stirred solution of 2-isopropylaminophenylmethanol (118 g, 0.71 mol) in toluene (800 mL) and the reaction mixture was heated to 117° C. for 4 h. The reaction mixture was allowed to cool to room temperature overnight and then filtered through a pad of Celite which was eluted with toluene. The filtrate was concentrated under reduced pressure to yield 2-isopropylaminobenzaldehyde (105 g, 90%) as an orange oil. 1H NMR (CDCl3; 300 MHz): 1.28 (d, 6H, CH(CH3)2), 3.76 (sept, 1H, CH(CH3)2), 6.65 (t, 1H, ArH), 6.69 (d, 1H, ArH), 7.37 (d, 1H, ArH), 7.44 (t, 1H, ArH), 9.79 (s, 1H, CHO).

Source