Ethanol → HCID 21440132, compound

HRID 328938Notes

Reaction equation

HRID 328938 reaction equation
O.[C:2]([C:10]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=1[OH:22])(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:23](O)[CH3:24]>>[C:2]([C:10]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][C:13]([C:14]([O:16][CH2:23][CH3:24])=[O:15])=[CH:12][C:11]=1[OH:22])(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 702EthanolHCID 131710720HCID 131710720, compound

Product 1

HCID 21440132HCID 21440132, compound

Procedure

A solution of 4-benzoyl-3-hydroxy-5-nitrobenzoic acid, monohydrate prepared as described in Example 1, step A, (100 g) in dry ethanol (2 liter) is evaporated in vacuo in order to remove the water of crystallization. The residue is redissolved in dry ethanol (2 liter), conc. sulfuric acid (45 ml) is added and the solution is refluxed for 20 hours. The excess of ethanol is removed in vacuo, and the residue is triturated with a saturated sodium hyrogen carbonate solution (about 900 ml). The resulting material is collected by filtration and washed with water. After drying and recrystallization from aqueous ethanol, ethyl 4-benzoyl-3-hydroxy-5-nitrobenzoate is obtained with a melting point of 167°-168° C.

Workup

  1. customis evaporated in vacuo in order
  2. customto remove
  3. customthe water of crystallization
  4. dissolutionThe residue is redissolved in dry ethanol (2 liter)
  5. additionconc. sulfuric acid (45 ml) is added
  6. temperaturethe solution is refluxed for 20 hours
  7. customThe excess of ethanol is removed in vacuo
  8. customthe residue is triturated with a saturated sodium hyrogen carbonate solution (about 900 ml)
  9. filtrationThe resulting material is collected by filtration
  10. washwashed with water
  11. customAfter drying
  12. customrecrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-a7608642810c4ae4aef6b38e456cc0d1
Source dataset
uspto-grants-1977_04
Patent number
US04018794

Reaction notes

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