Methanol → Methyl 4-amino-3,5-dichlorobenzoate

HRID 1502790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1502790
OS(O)(=O)=O.[NH2:6][C:7]1[C:15]([Cl:16])=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[Cl:17].[CH3:18]O>>[NH2:6][C:7]1[C:8]([Cl:17])=[CH:9][C:10]([C:11]([O:13][CH3:18])=[O:12])=[CH:14][C:15]=1[Cl:16]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 420614-Amino-3,5-dichlorobenzoic acid

Produkt 1

HCID 604808Methyl 4-amino-3,5-dichlorobenzoateAusbeute 70 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

conc. H2SO4 (2.5 mL, 97.04 mmol) was added drop wise to a stirred solution of 4-amino-3,5-dichlorobenzoic acid (10.0 g, 48.54 mmol) in MeOH (150 mL) at 0° C. and the reaction mixture was then stirred at 80° C. for 8 h. The volatiles were evaporated; ice-water was added to the residue and extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to afford the title compound as a white solid (7.5 g, 70%): 1H NMR (300 MHz, DMSO-d6) δ 8.05 (s, 2H), 3.96 (s, 3H); ESIMS m/z 282 ([M]+); IR (KBr): 1733, 762, 514 cm−1.

Aufarbeitung

  1. customThe volatiles were evaporated
  2. additionice-water was added to the residue
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-342532572b8d4abf9da7bf3db4ae01b7
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09210927B2

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