Sulfuric Acid → Benzoic acid, 3-formyl-4-hydroxy-, methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.FC(F)(F)[C:14](O)=[O:15].C1N2CN3CN(C2)CN1C3.S(=O)(=O)(O)O>O>[CH:14]([C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[OH:10])[C:3]([O:2][CH3:1])=[O:11])=[O:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Methyl-4-hydroxybenzoate (4.56 g, 30 mmol) was mixed with trifluoroacetic acid (24 ml) and hexamethylenetetramine (8.41 g, 60 mmol) (Duff reaction). The reaction medium was heated to 80° C. for three hours and cooled to 0° C., followed by successive addition of 15 ml of 50% sulfuric acid and 90 ml of demineralized water. After stirring for one hour at room temperature, the medium was extracted with ethyl ether, washed with water, dried over magnesium sulfate and filtered, and the solvents were evaporated off. The product was purified by passage through a column of silica and was eluted with dichloromethane. After evaporation of the solvents, 1.92 g of a crystallized white solid are obtained, equivalent to a yield of 36%. Its properties were as follows:
Workup
- temperaturecooled to 0° C.
- extractionthe medium was extracted with ethyl ether
- washwashed with water
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customthe solvents were evaporated off
- customThe product was purified by passage through a column of silica
- washwas eluted with dichloromethane
- customAfter evaporation of the solvents, 1.92 g of a crystallized white solid
- customare obtained, equivalent to a yield of 36%
Sources & evidence
- ORD record
- ord-631eadd522684fe1a88bfd7b8e0c289f
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06194450B1
Reaction notes
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