2-(Hydroxymethyl)-4-iodophenol → 5-Iodosalicylaldehyde

HRID 393312

反応式

HRID 393312 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH2:4][OH:5]>CC(C)=O.[O-2].[Mn+4].[O-2]>[OH:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH:4]=[O:5]

参加物

4

反応物 1

HCID 125452592-(Hydroxymethyl)-4-iodophenol

生成物 1

HCID 2526125-Iodosalicylaldehyde

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 180Acetone溶媒

実験手順

To a stirred solution of 2-hydroxy-5-iodobenzyl alcohol (43.5 g, 174.0 mmol) in acetone (700 mL) was added 85% activated manganese (IV) oxide (5 micron, 50 g, 494.0 mmol) and the solution stirred at room temperature for 16 hours. The manganese oxide was removed by filtration through diatomaceous earth and the filtrate concentrated in vacuo. The product was purified by flash silica chromatography (0-20% ethyl acetate in hexanes). The 2-hydroxy-5-iodobenzaldehyde was obtained as a greenish-yellow solid (24.3 g, 58%). A small amount of the 2-hydroxy-5-iodobenzaldehyde was recrystallized from methanol/water to afford an analytical sample and the remainder of the compound was used without further purification: mp 99-101° C. 1H NMR (CDCl3/300 MHz) 9.83 (s, 1H), 7.79 (d, 1H, J=2.2 Hz), 7.77 (dd, 1H, J=8.7 Hz, J=2.2 Hz), 6.81 (d, 1H, J=8.7 Hz). ESHRMS 246.9229 (M−H Calc'd 246.9256).

後処理

  1. customThe manganese oxide was removed by filtration through diatomaceous earth
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe product was purified by flash silica chromatography (0-20% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-069af8e587714270ba4689d4c2b9b142
出典データセット
uspto-grants-2004_10
特許番号
US06806288B1

関連ノート

読み込み中…