Methanol → Methyl 4-dimethylaminobenzoate

HRID 653029

Reaction equation

HRID 653029 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.OS(O)(=O)=O.[CH3:18]O>>[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:18])=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 120924-(Dimethylamino)benzoic acid

Product 1

HCID 70994Methyl 4-dimethylaminobenzoate

Procedure

p-Dimethylaminobenzoic acid (50 g.) and concentrated H2SO4 (25 ml.) in 350 ml. methanol were refluxed 18 hours. The reaction mixture was cooled, quenched with ice and water (350 ml.), neutralized portionwise with KHCO3 until foaming ceased, and extracted 3×200 ml. CHCl3. The organic layers were combined, washed 1×150 ml. brine, dried (MgSO4) and reduced in volume to yield crystalline title product, 52 g.; 1H-nmr: 3.02 (s, 6H), 3.87 (s, 3H), 6.66 (d, J=16Hz, 2H), 7.95 (d, J=16Hz, 2H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched with ice and water (350 ml.), neutralized portionwise with KHCO3 until foaming
  3. extractionextracted 3×200 ml
  4. washwashed 1×150 ml
  5. dry with materialbrine, dried (MgSO4)

Sources & evidence

ORD record
ord-3b163de5b6d64ca0a216d124d61c2d8b
Source dataset
uspto-grants-1987_06
Patent number
US04675186

Linked notes

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