Benzaldehyde → HCID 178516248, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:10](=[N:1]/[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1)\[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 4-amino-2-fluorophenol (1.27 g, 10 mmol) in 30 mL of toluene at room temperature under nitrogen in a Dean Stark apparatus was added benzaldehyde (1.01 ml, 10 mmol) followed by p-toluenesulfonic acid monohydrate (38 mg, 0.2 mmol). The mixture was heated to reflux for 4 hours. The reaction was cooled to room temperature and a solid crystallized out of the reaction mixture. The mixture was cooled to 0° C. and then filtered and the solids rinsed with toluene. The isolated tan crystals were dried under high vacuum (1.5 gm, 70% yield).