Formaldehyde → HCID 49874600, compound

Temperature

0 °C

The 4-chloro-5-isopropyl-2-methylphenol (5.0 g, 27.08 mmole) and magnesium chloride (3.87 g, 40.61 mmole) were mixed in acetonitrile (150 mL) and the mixture was cooled to 0° C. (ice bath). Triethylamine (10.28 g, 101.55 mmole) followed by para-formaldehyde (5.48 g, 182.79 mmole) were added to above mixture, which was stirred at 0° C. for 1 hour. The mixture was warmed to room temperature and then heated to 90° C. for 1 week. The contents were poured into water (100 mL) and extracted with EtOAc (2×100 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 (1.83 g, 32%): GCMS m/z 212.0 (M+).

1. additionwere added to above mixture, which
2. temperatureThe mixture was warmed to room temperature
3. temperatureheated to 90° C. for 1 week
4. extractionextracted with EtOAc (2×100 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-8b8452c920964bb2abba8a4dbfeddbef

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07259266B2