Dimethyl Sulfate → 3,4-Dimethoxy-2-nitrobenzaldehyde

HRID 354829노트

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HRID 354829 반응식
[C:1](=[O:4])([O-])[O-].[Na+].[Na+].O[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[C:10]([N+:16]([O-:18])=[O:17])[C:9]=1[O:19][CH3:20].S(OC)(OC)(=O)=O>C1(C)C=CC=CC=1>[CH3:20][O:19][C:9]1[C:10]([N+:16]([O-:18])=[O:17])=[C:11]([CH:14]=[CH:15][C:8]=1[O:4][CH3:1])[CH:12]=[O:13]

참가 물질

5

반응물 3

HCID 6497Dimethyl SulfateHCID 10340Sodium CarbonateHCID 96959Benzaldehyde, 4-hydroxy-3-methoxy-2-nitro-

생성물 1

HCID 1524373,4-Dimethoxy-2-nitrobenzaldehyde수율 78%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Anhydrous sodium carbonate (957 g., 9.03 moles), toluene (5 liters), 4-hydroxy-3-methoxy-2-nitrobenzaldehyde (1424 g., 7.22 moles) and dimethyl sulfate (810 ml., 8.67 moles) were refluxed for 4 hours. Toluene was removed in vacuo and the residual solid dissolved in 5 liters of ethyl acetate and 3 liters of water. The organic layer was separated, washed with 2 liters of 1 N NaOH and 6 liters of brine, decolorized with charcoal, dried over magnesium sulfate and filtered. Hexane (7.6 liters) was added slowly. After cooling in an ice bath, 1527 g. product was obtained by filtration. The crude material was recrystallized from ethanol to yield 1187 g. (78%) of the title compound as a pale yellow solid, 60°-62° C.

후처리

  1. customToluene was removed in vacuo
  2. dissolutionthe residual solid dissolved in 5 liters of ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with 2 liters of 1 N NaOH and 6 liters of brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. additionHexane (7.6 liters) was added slowly
  8. temperatureAfter cooling in an ice bath
  9. customproduct was obtained by filtration
  10. customThe crude material was recrystallized from ethanol
  11. customto yield 1187 g

출처 및 근거

ORD 기록
ord-92771050920449b3bf25cd04e17ea295
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04377581

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