3,6-DIMETHYL-2-HYDROXY BENZALDEHYDE

To a solution of 2, 5-dimethylphenol (7.0 g, 57.3 mmol) in acetonitrile (250 mL) were added triethylamine (30.1 mL, 0.212 mol) and magnesium chloride (8.17 g, 86 mmol). The mixture was stirred at room temperature for 15 minutes before adding paraformaldehyde (1 1 .5 g, 0.38 mol). The mixture was heated at 80°C for 20 hours. Acetonitrile was removed by evaporation in vacuo and a 10percent hydrochloric acid solution was added to the residue. The mixture was stirred at room temperature for 30 minutes and extracted with dichloromethane (2 x 40 mL). The organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (dichloromethane) to provide 3, 6-dimethyl-2- hydroxybenzaldehyde (27a) (3.56 g, 23.7 mmol, 42percent).Step 1: A suspension of 2, 5-dimethylphenol (1 ) (20 g, 160 mmol), paraformaldehyde (34 g, 1.1 mol), MgCIGeneral procedure: Aluminium trichloride (4.82 g, 36 mmol) was added to asolution of phenol (33 mmol) in anhydrous CH2Cl2 (50 mL)under argon, and the solution was stirred for 10 min.Dichloromethyl methyl ether (3.3 mL, 36 mmol) was addeddropwise via a syringe pump (7.7 mL/h). The reaction wasleft to stir for a further 10 min before cold H2O (200 mL) wasadded slowly. After stirring for a further 10 min, the organiclayer was separated and washed with brine (100 mL) andH2O (150 mL), dried over MgSO4, filtered, and concentratedto give the aldehyde which was purified by columnchromatography.

Molecular Weight:150.17
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:150.068079557
Monoisotopic Mass:150.068079557
Topological Polar Surface Area:37.3
Heavy Atom Count:11
Complexity:145
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes