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

HRID 725323ノート

反応式

HRID 725323 の反応式
[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.[I-].[Na+].[Si](Cl)(Cl)(Cl)Cl>C(#N)C.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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6342Acetonitrile溶媒

実験手順

A suspension of 17.2 g of ethyl 4-hydroxy-3-methoxy-5-nitrophenylglyoxylate in 100 ml 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).

後処理

  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

出典と根拠

ORDレコード
ord-aed7241c6d7749e2b094ed738b5a9752
出典データセット
uspto-grants-1998_01
特許番号
US05705703

反応ノート

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