Hydrochloric Acid → Ethyl 3-hydroxy-4-nitrobenzoate

HRID 1660175Notes

Reaction equation

HRID 1660175 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].Cl.[CH2:15](O)[CH3:16]>>[CH2:15]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([OH:1])[CH:3]=1)[CH3:16]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 692653-Hydroxy-4-nitrobenzoic acid

Product 1

HCID 12784564Ethyl 3-hydroxy-4-nitrobenzoateYield 1,492.2%

Procedure

3-Hydroxy-4-nitrobenzoic acid (20.0 g, 199 mmol) in ethanol (250 mg) was refluxed for 6 hr in the presence of dry hydrogen chloride (5 g). The solvent was evaporated and the residue was dissolved in methylene chloride. The solution was washed with sodium bicarbonate until the unreacted material was removed as a precipitate. The organic fraction was finally washed with brine, dried over magnesium sulfate to give a brown solid of 3-hydroxy-4-nitrobenzoic acid ethyl ester (17.1 g): mp 80°-81° C. (crystallized from diethyl ether-hexane); Anal. Calcd for C9H9NO5 : C, 51.19% H, 4.30% N, 6.6% and Found: C, 51.23% H, 4.30% N, 6.79%; ir(CHCl3) 3,260, 1,720, 1,535 and 1,320 cm-1 ; and nmr(CDCl3) δ1.35 (3H, t), 4.3 (2H, q), 7.7 (3H, m) and 10.4 (1H, s).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washThe solution was washed with sodium bicarbonate until the unreacted material
  4. customwas removed as a precipitate
  5. washThe organic fraction was finally washed with brine
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-2f4d5f4ee6fc4719bc8faf9cd60758b5
Source dataset
uspto-grants-1981_12
Patent number
US04307092

Reaction notes

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