Methanol → Methyl 4-aminobenzoate

HRID 59233

Reaktionsgleichung

Reaktionsgleichung von HRID 59233
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:16]O>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:16])=[O:7])=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 9784-Aminobenzoic AcidHCID 1118Sulfuric Acid

Produkt 1

HCID 12082Methyl 4-aminobenzoate

Versuchsvorschrift

To a solution of 4-amino benzoic acid (20.0 g, 0.14 mol) in methanol (400 mL) was added conc. sulphuric acid (40 mL). The reaction mass was stirred at RT for 6-7 h. The reaction mass was quenched with water and basified with NaHCO3 and extracted with DCM. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 15.0 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 3.72 (s, 3H), 5.96 (br s, 2H), 6.55 (d, J=8.1 Hz, 2H), 7.64 (d, J=8.4 Hz, 2H) MS (m/z): 152.21 (M+H)+.

Aufarbeitung

  1. customThe reaction mass was quenched with water
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a4b44a292bb54f48be8a7601f0af90a5
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09439890B2

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