2'-CHLORO-4'-HYDROXYACETOPHENONE

A solution of 2'-chloro-4'-methoxyacetophenone (18.5 g, 0.10 mol) and tosylmethylisocyanide (TOSMIC, 21.5 g, 0.11 mol) in dry 1, 2-dimethoxyethane (100 mL) was cooled to-10C. A solution of t-BuOK (22.4 g, 0.20 mol) in dry t-BuOH (250 mL) was added slowly keeping the temperature below 5C. The homogeneous orange solution was stirred for 2h/0C and lh/25C. The resulting suspension was evaporated to a slurry. Water (200 mL) was added and extracted with EtzO (3 x 150 mL). The organic phase was dried (Na2504) and the solvent was removed under reduced pressure leaving an orange oil. Yield : 19 g (97%). GCMS: > 98 % ; 1H-NMR (DMSO-d6) : 57. 49 (d, 1H), 7.12 (d, 1H), 7. 02 (dd, 1H), 4.42 (q, 1H), 3.80 (s, 3H), 1.55 (d, 3H).1 -(2-Chloro-4-methoxy-phenyl)-ethanoneTo a mixture of AICI3 (42.08 g; 315.60 mmol) in CH2CI2 (300 ml.) was added dropwise 3-chloroanisole (22.50 g; 157.80 mmol), at -300C. To the resulting mixture was added dropwise a solution of AcCI (10.50 ml 147.63 mmol) in CH2CI2 (100 ml.) at such a rate to keep the temperature below -15C. The resulting mixture was stirred for 4 hours at -100C. Subsequently, the mixture was poured onto ice and extracted with CH2CI2. The combined organic layers, were dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O/hexanes 1 :9) to afford 1 -(2-chloro-4-methoxy-phenyl)-ethanone (17.68 g).

Molecular Weight:184.62
XLogP3:2.4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:184.0291072
Monoisotopic Mass:184.0291072
Topological Polar Surface Area:26.3
Heavy Atom Count:12
Complexity:170
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes