Acetic Acid → 2-Amino-4-methoxybenzaldehyde

HRID 2079616

反応式

HRID 2079616 の反応式
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([N+:11]([O-])=O)[CH:4]=1.CCO.CC(O)=O.Cl>O.C([O-])([O-])=O.[Na+].[Na+].[Fe].CCOC(C)=O>[CH:7]([C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[NH2:11])=[O:8]

参加物

9

反応物 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 702EthanolHCID 3576914-Methoxy-2-nitrobenzaldehyde

生成物 1

HCID 3235032-Amino-4-methoxybenzaldehyde収率 98%

試薬・触媒・溶媒 4

HCID 23925Iron触媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 10340Sodium Carbonate溶媒

実験手順

A flask was charged with 4-methoxy-2-nitrobenzaldehyde (14.7 g, 81.2 mmol, 1.0 eq), EtOH (270 mL), glacial AcOH (270 mL), H2O (135 mL), degassed and filled with argon. Then Fe powder (325 mesh) (27.2 g, 0.49 mol, 6.0 eq) was added followed by addition of concentrated HCl (12.24 mL, 0.148 mol, 1.8 eq). After stirring the reaction mixture for 1 hour at 60-65° C. (oil bath) TLC (EtOAc/Hex=4:6) showed that no starting material was left. The reaction mixture was cooled down to RT, diluted with 200 mL of H2O and neutralized with Na2CO3 to pH=7-8. The product was extracted into CH2Cl2. The emulsion that formed was filtered through celite, organic layer was washed with brine, dried over Na2SO4, concentrated giving 12.0 g (98% yield) of the title compound.

後処理

  1. customdegassed
  2. additionfilled with argon
  3. waitwas left
  4. extractionThe product was extracted into CH2Cl2
  5. customThe emulsion that formed
  6. filtrationwas filtered through celite, organic layer
  7. washwas washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-03d2e85c79b64614a5514473c01273cc
出典データセット
uspto-grants-2011_04
特許番号
US07932262B2

関連ノート

読み込み中…