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

HRID 1503800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1503800
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 cold water was added to the residue and which was then 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 cold water was added to the residue and which
  3. extractionwas then extracted 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-a05d1961b0ed4661b8df8af3859556c1
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212164B2

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