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

HRID 27289

반응식

HRID 27289 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7f0110b15a4147a3a3aaf17c4792fba4
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04220801

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