Hydrochloric Acid → 2-Hydroxy-4-methylbenzaldehyde

Participants

Reaction Steps

109 μl (0.93 mmol) of tin-tetrachloride and 882 μl (3.70 mmol) of tri-n-butylamine were added to a solution of 1.0 g (9.25 mmol) of 3-methyl-phenol in toluene (12 ml) and the mixture was stirred for 30 min at RT. Then 611 g of paraformaldehyde were added and the resulting mixture was heated to 100° C. for 16 hours. After cooling to RT water (40 ml) was added and the pH was adjusted to 2 by addition of 1N HCl. This mixture was extracted with ether. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated. The residue was purified by column chromatography (silica gel; ether/cyclohexane 1:15) to yield 131 mg (10%) of 2-hydroxy-4-methyl-benzaldehyde as colorless crystals. 1HNMR (CDCl3, 300 MHz): δ 2.38 (s, 3H), 6.80 (s, 1H), 6.82 (d, J=7.9 Hz, 1H), 7.43 (d, J=7.9 Hz, 1H), 9.83 (s, 1H), 11.04 (s, 1H).

Provenance & Evidence