2-Methylresorcinol → 2,4-Dihydroxy-3-methylbenzaldehyde

HRID 55714

反応式

HRID 55714 の反応式
P(Cl)(Cl)(Cl)=O.CN([CH:14]=[O:15])C1C=CC=CC=1.[CH3:16][C:17]1[C:23]([OH:24])=[CH:22][CH:21]=[CH:20][C:18]=1[OH:19]>CCOCC>[OH:19][C:18]1[C:17]([CH3:16])=[C:23]([OH:24])[CH:22]=[CH:21][C:20]=1[CH:14]=[O:15]

参加物

5

反応物 3

HCID 118432-MethylresorcinolHCID 24813Phosphorus oxychlorideHCID 66737N-Methylformanilide

生成物 1

HCID 803952,4-Dihydroxy-3-methylbenzaldehyde収率 57%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Phosphorus oxychloride (80 mL, 0.86 mol) was added to a stirred mixture of N-methylformanilide (102 mL, 0.82 mol) in ether (250 mL). The mixture was stirred for 1 hour at room temperature and then cooled in ice. 2-Methyl resorcinol (Aldrich, 100 g, 0.81 mol) was added and the mixture was allowed to warm to room temperature while stirring overnight. The precipitated intermediate product was collected by filtration and rinsed with ether (3×). The intermediate was hydrolyzed by dissolving in a mixture of acetone (250 mL) and water (250 mL) and stirring for 30 minutes. Water (2 L) was added, the mixture was brought to a boil, and then allowed to cool and deposit crystalline product. This was recrystallized a second time from water (4 L) to afford pure product (70 g, 57%). M.p. 150° C. (Lit. 152°-3° C. [W. Baker et al., J. Chem. Soc. 2834-5 (1949)⟧

後処理

  1. temperaturecooled in ice
  2. temperatureto warm to room temperature
  3. stirringwhile stirring overnight
  4. filtrationThe precipitated intermediate product was collected by filtration
  5. washrinsed with ether (3×)
  6. dissolutionby dissolving in a mixture of acetone (250 mL) and water (250 mL)
  7. stirringstirring for 30 minutes
  8. additionWater (2 L) was added
  9. temperatureto cool
  10. customThis was recrystallized a second time from water (4 L)

出典と根拠

ORDレコード
ord-2272eae45ce6481684641bd9ff2d287f
出典データセット
uspto-grants-1997_04
特許番号
US05625081

関連ノート

読み込み中…