1-[3-(Phenylmethoxy)phenyl]ethanone

Yellow Liquid

3-Hydroxyacetophenone (136.15 g, 1 mol), potassium carbonate (414.63 g, 2 mol), KI (33.2 g, 0.2 mol), and benzyl bromide (171.04 g, 1 mol) were dissolved in acetone and the reaction mixture was refluxed while stirring for 24 hours, followed by washing with brine. The reaction mixture was extracted with ethyl acetate, the extract was dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography (ethyl acetate: hexane = 1: 3) to obtain 1-(3-benzyloxyphenyl) ethanone (221.8 g, yield 98 percent) in an oil state. [00470] To a stirred solution of 3-hydroxy acetophenone (1 g, 7.35 mmol) in acetone (25 mL) under inert atmosphere were added potassium iodide (244.1 mg, 1.47 mmol), potassium carbonate (2.02 g, 14.70 mmol) and benzyl bromide (1.5 g, 8.82 mmol) at RT. The reaction mixture was heated at 70 °C and stirred for 20 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the volatiles were evaporated under reduced pressure and the residue was diluted with water (30 mL) and extracted with EtOAc (2 x 30 mL). The combined organic extracts were washed with water (25 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography [Eluent: 7percent EtOAc/Hexanes] to afford l-(3- (benzyloxy)phenyl)ethanone (1.6 g, 69percent) as a colorless liquid. 1H NMR (400 MHz, DMSO-dTo a stirred solution of 3'-hydroxyacetophenone (LEQ) and benzyl bromide (1.5 eq) in dry DMF under N2, solid K2CO3 (2 eq) was added in one portion. The reaction mixture was stirred at 60° C for 3 days, then cooled down to room temperature. Most of the DMF was distilled off under reduced pressure. The residue was taken up in EtOAc and washed with 1N HC1, H20, Brine and dried (NA2SO4). Evaporation of the solvent under reduced pressure afforded a brown oil which was about a 1: 1 mixture of the starting material and the desired product. The latter was isolated by chromatography on silica gel (ETOAC/HEXANES, 1 : 1) affording the desired 3'-benzyloxy acetophenone (51percent). See for example: Schmidhammer, H.; Brossi, A. R Org. Chem. 1983, 48, 1469. TLC (silica gel, Ethyl acetate/hexanes 1: 2, vanillin stain): Rf= 0.58, orange brown (Rf starting material= 0.28). APOS;H NMR (CDCL3, 300MHZ) : 7.6-7. 1 (9H, m), 5.11 (2H, s, CH2PH) ; 2.59 (3H, s, CH3).

Molecular Weight:226.27
XLogP3:3.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:226.099379685
Monoisotopic Mass:226.099379685
Topological Polar Surface Area:26.3
Heavy Atom Count:17
Complexity:243
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes