Dimethyl Sulfate → Methyl 4-amino-5-chloro-2-hydroxybenzoate

HRID 846599

Reaktionsgleichung

Reaktionsgleichung von HRID 846599
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:12])[CH:3]=1.C[O-].[Na+].CO.S(OC)(O[CH3:22])(=O)=O>CO.O>[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([O:8][CH3:22])=[O:7])=[C:4]([OH:12])[CH:3]=1

Komponenten

6

Edukt 3

HCID 6497Dimethyl SulfateHCID 148832224-Amino-5-chloro-2-hydroxybenzoic acidHCID 23694274Sodium methanolate methanol

Produkt 1

HCID 14883223Methyl 4-amino-5-chloro-2-hydroxybenzoateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 4-amino-5-chloro-2-hydroxybenzoic acid (1.88 g, 0.010 mole) in absolute methanol (20 ml) was treated with 25% sodium methoxide/methanol (2.16 g, 0.010 mole), stirred for 30 minutes, and concentrated in vacuo. The solid residue was taken up in anhydrous acetone (30 ml), treated with dimethyl sulfate (1.64 g, 0.013 mole) and refluxed for 2 hours. The resultant solution was diluted with water (100 ml), and the precipitate was filtered, washed with water, and dried exhaustively in vacuo to afford 1.75 g (87%) of the title compound as fine colorless needles. The material was recrystallized from ethyl acetate/hexane; mp 138°-139° C.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. temperaturerefluxed for 2 hours
  3. filtrationthe precipitate was filtered
  4. washwashed with water
  5. customdried exhaustively in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b8028fed9620467b918409fb9488764d
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05137895

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