Methanol → Methyl 4-aminobenzoate

HRID 59233

Reaction equation

HRID 59233 reaction equation
[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

Participants

4

Reactant 3

HCID 887MethanolHCID 9784-Aminobenzoic AcidHCID 1118Sulfuric Acid

Product 1

HCID 12082Methyl 4-aminobenzoate

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-a4b44a292bb54f48be8a7601f0af90a5
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Linked notes

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