2,4-Dichloro-3-hydroxybenzaldehyde

Preparation 10 Preparation 8 2, 4-Dichloro-3-hvdroxy-benzaldehyde; Sec-butyllithium in cyclohexane (1.4M, 34.5ml, 48.3mmol) was added slowly to a solution of (2, 6-dichloro- phenoxy)-triethyl-silane (Preparation 7, 12.17g, 43.89mmol) in tetrahydrofuran (100ml) at -72Into a 250-mL 3-necked round-bottom flask, was placed a solution of 2, 4-dichloro-3- hydroxybenzaldehyde (5 g, 26.18 mmol, 1.00 eq.) in tetrahydrofuran (100 mL). This was followed by the addition of t-BuOK (2.94 g, 26.20 mmol, 1.00 eq.) in several batches at 0C. To this was added oxetan-2- one (2.08 g, 28.86 mmol, 1.10 eq.) dropwise with stirring at 0C. The resulting solution was stirred for 1 overnight at rt. The reaction was then quenched by the addition of 100 mL of water. The resulting solution was extracted with 10x50 mL of ethyl acetate and the water layers combined. The pH value of the solution was adjusted to 0-2 with hydrogen chloride (1 mol/L). The resulting solution was extracted with 2x50 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 1x20 mL of water and 1x20 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 : 10). This resulted in 690 mg (10%) of 3-(2, 6-dichloro-3- formylphenoxy)propanoic acid as a white solid.A 100-mL round-bottom flask was charged with

Molecular Weight:191.01
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:189.9588348
Monoisotopic Mass:189.9588348
Topological Polar Surface Area:37.3
Heavy Atom Count:11
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes