Methanol → Methyl 4-aminobenzoate

HRID 1927359Notes

Reaction equation

HRID 1927359 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1.[CH3:16]O>>[CH3:16][O:12][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][C:7]([NH2:6])=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 9784-Aminobenzoic AcidHCID 1118Sulfuric Acid

Product 1

HCID 12082Methyl 4-aminobenzoateYield 96%

Conditions

Temperature
0 °C

Procedure

Concentrated sulfuric acid was slowly added to a mixture of 4-aminobenzoic acid (4 g, 29.2 mmol) in methanol cooled to 0° C. After the addition, the mixture was stirred at room temperature for 5 hours. The mixture was washed with a saturated solution of sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated under vacuum to obtain 4-aminobenzoic acid methyl ester (49a) (4.22 g, 27.9 mmol, 96%) as an off-white solid.

Workup

  1. additionAfter the addition
  2. washThe mixture was washed with a saturated solution of sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1b216bd4c03b42e0a6d7338b16d29776
Source dataset
uspto-grants-2012_05
Patent number
US08183274B2

Reaction notes

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