Formaldehyde → HCID 818110, compound

Temperature

0 °C

The 4-hydroxy-3-methylbenzaldehyde (7.0 g, 51.41 mmole) and magnesium chloride (7.3 g, 77.12 mmole) were mixed in acetonitrile (100 mL) and cooled to 0° C. (ice bath). Triethylamine (19.51 g, 192.79 mmole) followed by para-formaldehyde (10.41 g, 347 mmole) were added to above mixture, which was stirred for 1 hour. The mixture was warmed to room temperature and then heated to 90° C. for 18 hours. The contents were poured into water (100 mL) and extracted with EtOAc (2 X 100 mL). The combined extracts were washed with brine (50 mL), dried over MgSO4, filtered and concentrated in vacuo to give an off-white solid which was subject to flash chromatography (silica gel) and eluted with 100% CH2Cl2 to give an off-white solid (2.2 g, 26%). GCMS m/z 164.0 (M+). 1H NMR (CDCl3/400 MHz) 11.82 (s, 1H), 9.96 (s, 1H), 9.89 (s, 1H), 7.96 (s, 1H), 7.92 (s, 1H), 2.32 (s, 3H).

1. additionwere added to above mixture, which
2. temperatureThe mixture was warmed to room temperature
3. temperatureheated to 90° C. for 18 hours
4. extractionextracted with EtOAc (2 X 100 mL)
5. washThe combined extracts were washed with brine (50 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto give an off-white solid which
10. washeluted with 100% CH2Cl2

ORD record

ord-6c5b3d2c1e224de68a6f9cb90c25d113

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07259266B2