[2-(Propan-2-ylamino)phenyl]methanol → 2-((Propan-2-yl)amino)benzaldehyde

HRID 12375

Reaction equation

[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][OH:12])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]=[O:12])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 117 °C

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).

Workup

temperatureto cool to room temperature overnight
filtrationfiltered through a pad of Celite which
washwas eluted with toluene
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-0b646f22560f477fb1da598dcb7191c5
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728006B2

Linked notes

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