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

HRID 274458Notes

Reaction equation

HRID 274458 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a019de595d5a4fe581d161a77629cb9f
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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