Hexamethylenetetramine → 5-Ethoxy-2-fluoro-4-hydroxy-benzaldehyde
Reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[OH:11])[CH3:2].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:24](O)=[O:25]>>[CH2:1]([O:3][C:4]1[C:5]([OH:11])=[CH:6][C:7]([F:10])=[C:8]([CH:9]=1)[CH:24]=[O:25])[CH3:2]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
The 2-ethoxy-5-fluoro-phenol (14.3 g) described in example 1.2 was dissolved in trifluoroacetic acid (90 ml). This solution was slowly added to a solution of hexamethylene tetramine (25.7 g) in trifluoroacetic acid (90 ml) at 80° C. The mixture was stirred for 1 h at 80° C. and concentrated. Water (250 ml) was added and stirred for 10 min. The mixture was neutralized with Na2CO3 and extracted with ether. The crude product was purified by column chromatography (n-hexane/ethyl acetate) to yield 9.43 g of 5-ethoxy-2-fluoro-4-hydroxy-benzaldehyde as a yellow solid. MS: 184 ([M]+).