Hydrochloric Acid → 7-Nitro-benzofuran-2-carboxylic acid

HRID 15448

反応式

HRID 15448 の反応式
O[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=O.[C:13](=[O:16])([O-])[O-:14].[K+].[K+].ClC[C:21](OC)=[O:22].[OH-].[K+].Cl>O.C1COCC1>[N+:10]([C:7]1[C:6]2[O:22][C:21]([C:13]([OH:14])=[O:16])=[CH:4][C:3]=2[CH:2]=[CH:9][CH:8]=1)([O-:12])=[O:11]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 668085-Nitrosalicylaldehyde

生成物 1

HCID 593413787-Nitro-benzofuran-2-carboxylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
130 °C

実験手順

3.0 g (17.9 mmol) of 2-hydroxy-5-nitrobenzaldehyde, 0.66 g (1.80 mmol) of tetra-N-butylammonium iodide and 9.92 g (71.81 mmol) of potassium carbonate are mixed, 4.09 g (37.7 mmol) of methyl chloroacetate are added and the mixture is heated at 130° C. for 4 h. 35 ml of THF and, with ice cooling, 6.04 g (107.71 mmol) of potassium hydroxide are added. Following the addition of 50 ml of water, the mixture is stirred at RT for 20 h. Using concentrated hydrochloric acid, the pH is adjusted to 0. The mixture is extracted with ethyl acetate. The organic phase is washed with water and dried over sodium sulfate. After the addition of silica gel, the mixture is concentrated and chromatographed on silica gel (mobile phase gradient: toluene to toluene/methanol/glacial acetic acid 35:5:1). Concentration of the product fractions and drying under reduced pressure gives 2.00 g (54% of theory) of the title compound.

後処理

  1. extractionThe mixture is extracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. additionAfter the addition of silica gel
  5. concentrationthe mixture is concentrated
  6. customchromatographed on silica gel (mobile phase gradient: toluene to toluene/methanol/glacial acetic acid 35:5:1)
  7. customConcentration of the product fractions and drying under reduced pressure

出典と根拠

ORDレコード
ord-3e7ea17bb8324136bb3b914101eff4d0
出典データセット
uspto-grants-2010_06
特許番号
US07732477B2

関連ノート

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