Hydrochloric Acid → Ethyl 3-hydroxy-4-nitrobenzoate

HRID 127003

Reaktionsgleichung

Reaktionsgleichung von HRID 127003
[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]

Komponenten

4

Edukt 3

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

Produkt 1

HCID 12784564Ethyl 3-hydroxy-4-nitrobenzoateAusbeute 1.492,2 %

Versuchsvorschrift

3-Hydroxy-4-nitrobenzoic acid (20.0 g, 109 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, 6.63% 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)δ 1.35 (3H, t), 4.3 (2H, q), 7.7 (3H, m) and 10.4 (1H, s).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7c14fff95d394707845974cae316b863
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04254118

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