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2-hydroxybenzaldehyde O-methyloxime → Methyl 2-(2-methoxyiminomethylphenoxymethyl)phenylglyoxylate O-methyloxime

HRID 374305
노트
인쇄 미리보기

반응식

HRID 374305 반응식
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11].C[O-].[Na+].[CH3:15][O:16][N:17]=[C:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29]Br)[C:19]([O:21][CH3:22])=[O:20]>CO.CN(C)C=O.C(OCC)(=O)C>[CH3:15][O:16][N:17]=[C:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][O:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH:4]=[N:3][O:2][CH3:1])[C:19]([O:21][CH3:22])=[O:20]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 5232402-hydroxybenzaldehyde O-methyloximeHCID 10942334Sodium MethoxideHCID 54028047Methyl 2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate

생성물 1

HCID 53961752Methyl 2-(2-methoxyiminomethylphenoxymethyl)phenylglyoxylate O-methyloxime

시약·촉매·용매 3

HCID 887Methanol용매
HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

3.0 g (20 mmol) of 2-hydroxybenzaldehyde O-methyloxime are dissolved in 20 ml of methanol, and 3.6 g (20 mmol) of sodium methanolate (30% strength in methanol) are added. The mixture is refluxed for four hours and then concentrated. The residue is taken up in 100 ml of dimethylformamide, and 6.5 g (23 mmol) of methyl 2-bromomethylphenylglyoxylate O-methyloxime in 50 ml of dimethylformamide are added. The mixture is stirred at 100° C. for 5 hours, the solvent is stripped off, and the residue is taken up in ethyl acetate. The organic phase is washed with water, dried and concentrated. The residue is triturated with pentane to induce crystallization. 4.8 g (67% of theory) of the title compound are obtained in the form of colorless crystals (melting point 73°-76° C., compound no. 2).

후처리

  1. temperatureThe mixture is refluxed for four hours
  2. concentrationconcentrated
  3. washThe organic phase is washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is triturated with pentane
  7. customcrystallization

출처 및 근거

ORD 기록
ord-a603bb90994b49609cfa9dee60e5aa27
출처 데이터셋
uspto-grants-1992_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05166399

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