(Z)-Benzaldehyde oxime → 2,3-Dichloro-4-(4-hydroxybenzoyl)phenoxyacetic acid

HRID 27289

反応式

HRID 27289 の反応式
[H-].[Na+].C(=N[OH:11])C1C=CC=CC=1.[H][H].[Cl:14][C:15]1[C:25]([Cl:26])=[C:24]([C:27](=[O:37])[C:28]2[CH:33]=[CH:32][C:31]([N+]([O-])=O)=[CH:30][CH:29]=2)[CH:23]=[CH:22][C:16]=1[O:17][CH2:18][C:19]([OH:21])=[O:20]>CN(C=O)C>[Cl:14][C:15]1[C:25]([Cl:26])=[C:24]([C:27](=[O:37])[C:28]2[CH:33]=[CH:32][C:31]([OH:11])=[CH:30][CH:29]=2)[CH:23]=[CH:22][C:16]=1[O:17][CH2:18][C:19]([OH:21])=[O:20]

参加物

6

反応物 4

HCID 12143(Z)-Benzaldehyde oximeHCID 24758Sodium hydrideHCID 203936952,3-Dichloro-4-(4-nitrobenzoyl)phenoxyacetic acidHCID 178418361HCID 178418361、化合物

生成物 1

HCID 128540042,3-Dichloro-4-(4-hydroxybenzoyl)phenoxyacetic acid収率 88%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In the above described equipment, 0.312 g. of sodium hydride in 17.5 ml. of DMF is stirred while dropwise adding 0.874 ml. of benzaldoxime. The exothermic reaction forms a heavy precipitate while generating hydrogen gas. When the H2 -evolution ceases, 1,4806 g. of 2,3-dichloro-4-(4-nitrobenzoyl)phenoxyacetic acid is added, which will start H2 -evolution again and produce a homogenous dark solution. Upon further stirring, a precipitate starts to form which after several hours may become heavy enough to interfere with the magnetic stirrer. After 15 hours, the mixture is diluted with 175 ml. of water and filtered. By acidifying the filtrate with concentrated HCl to a pH of 2, a milky oil separates which solidifies upon standing. After collecting the crystalline material by filtration, washing it with cold water and drying it at 60° C. under house vaccum, 1.1986 g. (88% of theory) of 2,3-dichloro-4-(4-hydroxybenzoyl)phenoxyacetic acid is obtained.

後処理

  1. additionwhile dropwise adding 0.874 ml
  2. customThe exothermic reaction forms a heavy precipitate
  3. customproduce a homogenous dark solution
  4. customto form which after several hours
  5. additionthe mixture is diluted with 175 ml
  6. filtrationof water and filtered
  7. customAfter collecting the crystalline material
  8. filtrationby filtration
  9. washwashing it with cold water
  10. customdrying it at 60° C. under house vaccum, 1.1986 g

出典と根拠

ORDレコード
ord-7f0110b15a4147a3a3aaf17c4792fba4
出典データセット
uspto-grants-1980_09
特許番号
US04220801

関連ノート

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