Réaction #51206

Équation de réaction

HCl

paraformaldehyde

3-methyl-phenol

SnCl4

→

title product

Rendement 25.5%

2-Hydroxy-4-methyl-benzaldehyde

Rendement 25.5%

Solvants

water

toluene

Conditions de réaction

Traitement

1. 1
   ExtractionThe solution was extracted with ether (25 ml)
2. 2
   Lavagewashed with brine (20 ml)
3. 3
   Séchagedried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Autreevaporated to a brown oil
6. 6
   AutreThis oil was purified by column chromatography

Mode opératoire

To a stirred solution of 3-methyl-phenol (1 g, 9.2 mmol) in toluene (5 ml) at room temperature under nitrogen was added SnCl4 (241 mg, 0.92 mmol) and tri-nbutylamine (0.6 ml, 2.77 mmol). After 20 min, paraformaldehyde (611 mg, 20.3 mmol) was added and the whole stirred at 100° C. for 16 h. The reaction mixture was diluted with water (20 ml) and acidified with 2N HCl to pH2. The solution was extracted with ether (25 ml), washed with brine (20 ml), dried (MgSO4) filtered and evaporated to a brown oil. This oil was purified by column chromatography using 5% EtOAc in pentane as eluant to provide the title product (319 mg, 25%); 1HNMR (400 MHz, CDCl3) δ: 2.3 (s, 3H), 6.75 (m, 2H), 7.35 (d, 1H), 9.75 (s, 1H), 11.00 (s, 1H).

Source