Dimethylformamide dimethyl acetal → 2-Nitro-5-phenoxybenzaldehyde

HRID 390207

反応式

HRID 390207 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:5]=1[CH3:17])([O-:3])=[O:2].C[O:19]C(OC)N(C)C>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:5]=1[CH:17]=[O:19])([O-:3])=[O:2]

参加物

4

反応物 2

HCID 78373Dimethylformamide dimethyl acetalHCID 27284182-Nitro-5-phenoxytoluene

生成物 1

HCID 442030822-Nitro-5-phenoxybenzaldehyde

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 2-nitro-5-phenoxytoluene (57.3 g, 0.25 mol) prepared in Step A above and dimethylformamide dimethyl acetal (43.1 mL, 0.324 mol) in DMF (259 mL) was heated overnight at 140° C. The mixture was cooled to room temperature, and the solvent was evaporated in vacuo. The residue was dissolved in THF (500 mL) and transferred to a 3 L 3-neck flask equipped with an overhead stirrer. The mixture was diluted with 500 mL of water, and NalO4 (160 g, 0.75 mol) was added in portions (slight exotherm). The mixture was stirred overnight at room temperature. The solids were filtered and washed well with EtOAc. The filtrate was washed 3× with saturated aqueous NaHCO3 solution, and then dried (MgSO4). The solution was filtered and the solvent was evaporated in vacuo. The crude product was chromatographed (10-40% CH2Cl2:hexane) to yield 2-nitro-5-phenoxy-benzaldehyde as a yellow crystalline solid.

後処理

  1. customthe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in THF (500 mL)
  3. customequipped with an overhead stirrer
  4. additionThe mixture was diluted with 500 mL of water, and NalO4 (160 g, 0.75 mol)
  5. additionwas added in portions (slight exotherm)
  6. filtrationThe solids were filtered
  7. washwashed well with EtOAc
  8. washThe filtrate was washed 3× with saturated aqueous NaHCO3 solution
  9. dry with materialdried (MgSO4)
  10. filtrationThe solution was filtered
  11. customthe solvent was evaporated in vacuo
  12. customThe crude product was chromatographed (10-40% CH2Cl2:hexane)

出典と根拠

ORDレコード
ord-c8f62cee32af40b19ec672e9e3b30e34
出典データセット
uspto-grants-2013_02
特許番号
US08383637B2

関連ノート

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