5′-Chloro-2′-hydroxyacetophenone

slightly yellow crystalline powder or chunks

p-Chlorophenyl acetate 2c (10 gm, 0.091mol) was in 500 mL round bottom flask containing aluminium chloride (14.56 gm, 0.11 mol). It was heated on an oil bath at 140-150 °C for 5-6 hr. The progress of the reaction was monitored by TLC using ethyl acetate:hexane as a solvent system. The reaction mixture was quenched with crushed ice and obtained solid product was extracted with ethyl acetate (2×50 mL). The organic extracts were washed with brine solution (2×15 mL) and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to afford the corresponding crude compound. The obtained crude compound 3c was recrystallized using aq. ethanol. Yield 90percent. M.p. 54-56 °C.General procedure: O-Acyloxy benzenes (0.28 mmol) were dissolved in TfOH (3 ml) at 0 °C. The reaction mixture was warmed to room temperature for appropriate time in Table 3, then poured into cold water and ethyl acetate. The organic layer was washed with 1 M HCl, saturated NaHCO4-chlorophenyl acetate (2) (0.1 mole) and anhydrous aluminum trichloride (0.11 mole) were mixed thoroughly in a round bottom flask. The reaction mixture was heated gradually at 120°C till HCl gas was completely exhausted. The heating was extended for 2 hours at 160°C. The progress and completion of the reaction was monitored by TLC. At the end of the reaction the resulting aluminum complex was decomposed from crushed ice containing little amount of hydrochloric acid. The crude product was filtered dried and crystallized from methanol. Yield 60percent, m. p. 53-55 °C (Reported m.p. 53°C).General procedure: A mixture of allyl phenyl ethers 1 (1 mmol) and iodine (20 molpercent) in polyethylene glycol-400(10 mL) was stirred at room temperature for 25-30 minutes. The reaction mixture was poured incold solution of sodium thiosulphate and extracted by ethyl acetate. The combine organic layerwas dried over anhydrous Na2SO4 and evaporated under vacuum and purified by columnchromatography. The corresponding product was obtained in 86-96percent yield.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) of photosensitizer and 2.80 mg (6 × 10 -3 mmol) of cobalt catalyst were charged, the atmosphere was replaced with Ar atmosphere, and then0.2 mmol of 3'-chloroacetophenone (R1 is COCH3, R3 is Cl, R2, R4 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 points. Nuclear magnetic resonance spectroscopy and mass spectrometry identification of broad-based as 3 '- chloro -2_ hydroxyacetophenone, 3' - chloro -4_ light base acetophenone and 3 '- chloro-6_Hydroxyacetophenone.The conversion of 3'-chloroacetophenone was 43percent. The conversion of 3'-chloro-2-hydroxyacetophenone, 3'-chloro-4-hydroxyacetophenone and 3'-chloro-6-hydroxyacetophenone The yields were 6percent, 2percent and 34percent respectively, and the H2 yield was 42percent.

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