Sodium Iodide → Benzeneacetic acid, 3,4-dihydroxy-5-nitro-alpha-oxo-, ethyl ester

HRID 2254728노트

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HRID 2254728 반응식
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][C:3]=1[O:18]C.C(#N)C.[I-].[Na+].[Si](Cl)(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[OH:18][C:3]1[CH:4]=[C:5]([C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[OH:1]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 24816Silicon tetrachlorideHCID 14450984Ethyl 4-hydroxy-3-methoxy-5-nitrophenylglyoxylate

생성물 1

HCID 5747976Benzeneacetic acid, 3,4-dihydroxy-5-nitro-alpha-oxo-, ethyl ester

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A suspension of 17.2 g of ethyl 4-hydroxy-3-methoxy-5-nitrophenylglyoxylate in 100 of dry acetonitrile and 100 ml of dry toluene is treated with 10.53 g of sodium iodide and 11.9 g of silicon tetrachloride and heated under reflux for 47 hours. The reaction mixture is then evaporated and the residue is distilled six times with 200 ml of toluene each time. The residue obtained is partitioned between water and ether and filtered through a filter aid of diatomaceous earth. The ethereal phase is washed four times with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated. The oily residue is treated three times with ether and active carbon. There is obtained ethyl 3,4-dihydroxy-5-nitrophenylglyoxylate of m.p. 77°-79° (from ether/n-hexane).

후처리

  1. temperatureheated
  2. temperatureunder reflux for 47 hours
  3. customThe reaction mixture is then evaporated
  4. distillationthe residue is distilled six times with 200 ml of toluene each time
  5. customThe residue obtained
  6. customis partitioned between water and ether
  7. filtrationfiltered through a filter aid of diatomaceous earth
  8. washThe ethereal phase is washed four times with saturated sodium chloride solution
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. additionThe oily residue is treated three times with ether and active carbon

출처 및 근거

ORD 기록
ord-5dce6a7decac409992f0d627b093b512
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05236952

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