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With potassium carbonate; potassium iodide In acetone for 24 h; Heating / reflux
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. 1H NMR (200MHz, CDC13): No. 7.59-7.53 (m, 2H), 7.44-7.33 (m, 6H) 7.19 (m, 1H), 5.11 (s, 2H), 2.6 (s, 3H).
69%
With potassium carbonate; potassium iodide In acetone at 70℃; for 20 h;
[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-d6): δ 7.55-7.51 (m, 2H), 7.45-7.25 (m, 7H), 5.16 (s, 2H), 2.55 (s, 3H).
51%
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 60℃; for 72 h;
To 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).
Reference：
[1] Patent: WO2005/100303, 2005, A1, . Location in patent: Page/Page column 45
[2] Patent: US5716984, 1998, A,
[3] Patent: US5817693, 1998, A,
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[8] Patent: WO2015/191630, 2015, A1, . Location in patent: Paragraph 00470
[9] Patent: WO2004/48365, 2004, A1, . Location in patent: Page 58
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[15] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 16, p. 4661 - 4665
[16] Journal of Enzyme Inhibition and Medicinal Chemistry, 2011, vol. 26, # 5, p. 643 - 648
[17] Organic Process Research and Development, 2007, vol. 11, # 5, p. 825 - 835
2
[ 121-71-1 ]
[ 100-44-7 ]
[ 34068-01-4 ]
Yield
Reaction Conditions
Operation in experiment
86%
With potassium carbonate; triethylamine In acetone
EXAMPLE 1 3-Benzyloxyacetophenone A mechanically stirred mixture of 1 kg. (7.35 mole) of 3-hydroxyacetophenone, 1.035 kg. (7.5 mole) anhydrous potassium carbonate and 0.945 kg. (7.5 mole) of benzylchloride in 4.1 of acetone was heated at reflux for 24 hours after which 0.1035 kg. (0.75 mole) portion of potassium carbonate and 0.0945 kg. (0.75 mole) portion of benzylchloride were added and refluxing continued. This addition was repeated after 72 hours of refluxing and refluxing continued for 96 hours. The reaction was cooled, filtered and the filtrate concentrated on a rotovapor. The filtrate was then treated with 0.202 kg. (2.0 mole) triethylamine and stirred overnight. The reaction was diluted with 1 liter ether and filtered. The filtrate was evaporated and the residue distilled to yield 1.429 kg. (86percent) of the title compound as an oil. BP 160° C. (0.3 torr). IR (CHCl3) 1695, 1605, 1595, 1493 and 1433 cm-1. PMR (CDCl3) δ2.52 (s, CH3), 5.03 (s, CH2) and 7.0-7.7 (m, Ph).
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2491 - 2500
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[8] Patent: WO2006/67416, 2006, A1, . Location in patent: Page/Page column 37
[9] Patent: WO2006/67412, 2006, A1, . Location in patent: Page/Page column 35
[10] Patent: US4360700, 1982, A,
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[12] Patent: US2109458, 1936, ,
3
[ 121-71-1 ]
[ 53772-44-4 ]
[ 34068-01-4 ]
Reference：
[1] Journal of the American Chemical Society, 2004, vol. 126, # 23, p. 7359 - 7367
4
[ 121-71-1 ]
[ 7732-18-5 ]
[ 584-08-7 ]
[ 100-44-7 ]
[ 34068-01-4 ]
Reference：
[1] Patent: US4404222, 1983, A,
[2] Patent: US4407819, 1983, A,
5
[ 100-39-0 ]
[ 34068-01-4 ]
Reference：
[1] European Journal of Organic Chemistry, 2017, vol. 2017, # 1, p. 39 - 44
4-{3-[6-{3-[4-<i>tert</i>-butoxycarbonyl-2-(2-<i>tert</i>-butoxycarbonyl-ethyl)-butyryl]-phenoxycarbonyl}-4-(3-hydroxy-benzoyl)-hexanoyloxy]-benzoyl}-heptanedioic acid di-<i>tert</i>-butyl ester[ No CAS ]
4-[3-(4-(3-benzyloxy-benzoyl)-6-{3-[4-<i>tert</i>-butoxycarbonyl-2-(2-<i>tert</i>-butoxycarbonyl-ethyl)-butyryl]-phenoxycarbonyl}-hexanoyloxy)-benzoyl]-heptanedioic acid di-<i>tert</i>-butyl ester[ No CAS ]
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