1-(4-Chloro-2-hydroxyphenyl)ethanone

i) 4-Chloro-2-hydroxyacetophenone In a 500 mL of round bottom flask purged with argon was placed 26.00 g (0.153 mol) of 3-acetoxychlorobenzene, cooled with ice bath. Then 30.00 g (0.225 mol) of AlCl3 was added in portions. The resulting mixture was heated to 140° C. for 2 h (caution: vigorous evolution of gas) and then cooled to 0° C. treated with 15 mL of conc. HCl in 100 mL of ice water, extracted with EtOAc (3.x.300 mL). The combined organic extracts were washed with brine and dried (Na2SO4). Removal of the solvent gave 24.00 g (92percent) of the title compound as a light yellow liquid: 1H NMR (250 MHz, CDCl3) d 10.7 (s, 1H), 7.65 (d, J=8.6 Hz, 1H), 6.98 (d, J=1.8 Hz, 1H), 6.87 (dd, J=1.8, 8.6 Hz, 1H), 2.61 (s, 3H).4-Chloro-2-hydroxyacetophenone.; 3-Chlorophenyl acetate (10 g, 0.0588 mol) was heated together with aluminum chloride (13.86 g, 0.105 mol) at 160 °C for 2 hours. The mixture was poured on water and extracted with diethylether. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure. The residue was dissolved in methanol. The solution was treated with charcoal, filtered and water was added to the filtrate. The resulting oil was extracted with diethylether. The organic layer was dried over magnesium sulfate and diethylether was evaporated under reduced pressure. The resulting oil was used without further purification (77 percent). IR (KBr) : u : 3436 (O-H), 3073 (C-H aromatic), 1643 (C=O) cni 1.1-methyl-3-cyanoquinoline salt as a photosensitizer, Cobalt oxime complex 2 as a cobalt catalyst, 5mL of acetonitrile was added2.69 mg (1 × 10 -2 mmol) photosensitizer and 2.80 mg (6 × 10 -3 mmol) cobalt catalyst, Replacing the atmosphere with Ar atmosphereAnd then0.2 mmol of 4'-chloroacetophenone (R1 is COCH3, R4 is Cl, R2, R3 are independently H) and 2 mmol of H2O are added. Room temperature, high pressureMercury lamp irradiation 5h. After the reaction was completed, the H2 production was detected by GC (TCD) and the conversion of benzene by GC (FID), Then over the column pointsfrom. 1H NMR and MS identified products were 4'-chloro-2'-hydroxyacetophenone and 4'-chloro-3'-hydroxyacetophenone. The conversion of 4'-chloroacetophenone was 56percent, the yields of 4'-chloro-2'-hydroxyacetophenone and 4'-chloro-3'-hydroxyacetophenone were 14percent and 42percent, H2 yield of 56percent.

Molecular Weight:170.59
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:170.0134572
Monoisotopic Mass:170.0134572
Topological Polar Surface Area:37.3
Heavy Atom Count:11
Complexity:158
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes