4-Chlorophthalide

To a solution of 3-chloro-2-formylbenzoic acid (24 g, 91.0 mmol) in methanol (250 mL) was added NaBH4 (5.14 g, 136 mmol). The reaction was stirred at ambient temperature for 2 h. The mixture was concentrated to dryness to provide 3-chloro-2-(hydroxymethyl)benzoic acid as a yellow oil. To the oil in THF (80 mL) was added hydrogen chloride in dioxane (6N, 20 mL). The mixture was stirred at ambient temperature for 2 h and then extracted with EtOAc (3*50 mL). The combined organic phase was dried over sodium sulfate, filtered and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (PE/EtOAc=5/1) to provide

Molecular Weight:168.57
XLogP3:2
Hydrogen Bond Acceptor Count:2
Exact Mass:167.9978071
Monoisotopic Mass:167.9978071
Topological Polar Surface Area:26.3
Heavy Atom Count:11
Complexity:181
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes