2-Chloro-3,4-dimethoxybenzaldehyde

beige-yellow to beige crystalline powder

General procedure: Following an adaptation of the procedure of McKillop et al.7, anaqueous solution of 1.20 g of NaOH (30 mmol, 3.0 eq.) in 50 mL of deionized water was added to astirring solution of 2.31 g (10 mmol) of 2-bromo-isovanillin (2-bromo-3-hydroxy-4-methoxybenzaldehyde)in 50 mL of dichloromethane. Next, phase transfer catalyst was added, as 3.40 g of eithertetrabutylammonium hydrogen sulfate (TBAHS, 10.0 mmol, 1.0 eq.) or recycled catalyst (assuming thatthe recovered catalyst is tetrabutylammonium hydroxide, 2.6 g is 10 mmol, 1.0 eq). Once dissolved, 17g (120 mmol, 12 eq.) of methyl iodide was then added to the mixture and the reaction was allowed tostir at room temperature. Reaction progress was monitored by HPLC. As monitored by HPLC, reactionprogress generally showed complete turnover to product with no side products by 3 hours, however thesolution was typically allowed to stir overnight for convenience. The reaction mixture was extracted with3 x 50 mL portions of CH2Cl2. The combined organic extracts were washed with brine and deionizedwater, dried over MgSO4, filtered, and concentrated by evaporation under reduced pressure to yield aeither a white or yellow solid. To remove catalyst, the solid was first ground to a fine powder with amortar and pestle. This solid was poured on top of a 2 – 3 cm layer of dry silica gel in a 3 – 4 cm (I.D.)sintered glass fritted Buchner funnel. The solid was extracted with 1:5 ethyl acetate:hexanes in 75 mLportions by pouring the solvent mixture over the dry solids with vacuum suction to collect the solutionin a round bottom flask. Allow the solids to dry between solvent portions for best separation. The first1250 mL typically contained 85 - 95percent of pure product. The combined eluent was evaporated to drynessunder reduced pressure to afford a dense, white, flakey solid (2.06 g, 90percent). If the product was found tocontain non-halogenated contaminants from the previous step, pure halogenated product was easilyobtained by recrystallization from hexanes. The phase transfer catalyst, presumably a mixture oftetrabutylammonium salts, was recovered by either scooping it out of the filter or by eluting with ethylacetate.Step 2--Formation of 2-Chloro-3, 4-dimethoxybenzaldehyde Step 2

Molecular Weight:200.62
XLogP3:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:200.0240218
Monoisotopic Mass:200.0240218
Topological Polar Surface Area:35.5
Heavy Atom Count:13
Complexity:174
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes