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

HRID 12375

反応式

HRID 12375 の反応式
[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]

参加物

4

反応物 1

HCID 10797123[2-(Propan-2-ylamino)phenyl]methanol

生成物 1

HCID 110410352-((Propan-2-yl)amino)benzaldehyde収率 90.6%

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
117 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-0b646f22560f477fb1da598dcb7191c5
出典データセット
uspto-grants-2010_06
特許番号
US07728006B2

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