Sulfuric Acid → Methyl 4-dimethylaminobenzoate

HRID 1904031

Reaction equation

HRID 1904031 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[C:18](=O)(O)[O-].[Na+]>CO>[CH3:18][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([N:2]([CH3:12])[CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 120924-(Dimethylamino)benzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 70994Methyl 4-dimethylaminobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

23 g of 4-dimethylaminobenzoic acid was dissolved in 200 ml of methanol to which was added 2 ml of concentrated sulfuric acid and the mixture was refluxed with heating for 2 days. After cooling, the reaction mixture was poured into an aqueous solution of sodium bicarbonate and the crystals thus deposited were collected by filtration, washed with water and dried to obtain 24 g of 4-dimethylaminobenzoic acid methyl ester having a melting point of 101° to 102° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 2 days
  3. temperatureAfter cooling
  4. filtrationthe crystals thus deposited were collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-05ee31fdce14478aabec7f1a824e6376
Source dataset
uspto-grants-1984_03
Patent number
US04439519

Linked notes

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