Hydrochloric Acid → 2-Hydroxy-4-methylbenzaldehyde

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).

1. temperaturethe resulting mixture was heated to 100° C. for 16 hours
2. additionwas added
3. extractionThis mixture was extracted with ether
4. washThe combined organic extracts were washed with brine
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. customThe residue was purified by column chromatography (silica gel; ether/cyclohexane 1:15)

ORD record

ord-91f30f60956241e38e52c14e2a903061

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07674815B2