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Chemical Structure| 22545-14-8 Chemical Structure| 22545-14-8

Structure of 22545-14-8

Chemical Structure| 22545-14-8

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Product Details of [ 22545-14-8 ]

CAS No. :22545-14-8
Formula : C10H14O2
M.W : 166.22
SMILES Code : CCOC1=CC=CC=C1CCO
MDL No. :MFCD11592442

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Application In Synthesis of [ 22545-14-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 22545-14-8 ]

[ 22545-14-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 7768-28-7 ]
  • [ 75-03-6 ]
  • [ 22545-14-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 70℃; 4.4 g of 2-hydroxyphenethyl alcohol was dissolved in 80 ml of N, N-dimethylformamide, and 15. 3 g of ethyl iodide and 4 . 7 g of potassium carbonate were added. After stirring was continued at 70°C overnight, the solution was diluted with ethyl acetate, and washed successively with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was purified by silica gel column chromatography, to give 3.2 g of the title compound in the 4:1 hexane-ethyl acetate fraction.1H-NMR (CDCl3) delta: 1.43 (t, J=6.8Hz, 3H) 2.92 (t, J=6.0Hz, 2H) 3.85 (br, 2H) 4. 05 (q, J=6.8Hz, 2H) 6.85-6.91 (m, 2H) 7.15-7.22 (m, 1H)
  • 2
  • [ 7768-28-7 ]
  • [ 22545-14-8 ]
  • [ 75-03-6 ]
  • [ 124-63-0 ]
  • [ 61850-95-1 ]
YieldReaction ConditionsOperation in experiment
With lithium bromide; potassium carbonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide; acetone; Step A: Preparation of ethoxyphenethyl bromide STR30 To a suspension of 1.00 g (7.24 mmol) of 2-hydroxyphenethyl alcohol and 1.35 g (8.68 mmol) of potassium carbonate in 15 ml of N,N-dimethylformamide was added 2.00 g (14.48 mmol) of iodoethane at 0° C. The reaction mixture was stirred at 40-45° C. for 12 h and was poured into 200 ml of ether. It was washed with water (20 ml *3), dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography with 9:1 hexane/ethyl acetate to afford the 2-ethoxyphenethyl alcohol as a colorless oil. To a solution of 1.35 g (8.12 mmol) of 2-ethoxyphenethyl alcohol and 2.05 g (20.03 mmol) of triethylamine in 15 ml of dichloromethane was slowly added 1.86 g (16.24 mmol) of methanesulfonyl chloride at 0° C. The reaction mixture was stirred at 0° C. for 2 h and was poured into 200 ml of mixed solution of hexanelether(1:1). It was washed with 30 ml of water, dried over MgSO4, filtered through a plug of silica gel and concentrated. The residue was dissolved in 30 ml of acetone and 2.82 g (32.48 mmol) of lithium bromide was added slowly at 0° C. The reaction mixture was refluxed for 5 h and volatiles were removed. The residue was added 150 ml of ether, washed with water (30 ml *2), dried over MgSO4, filtered through a plug of silica gel and concentrated to give 2-ethoxyphenethyl bromide as a colorless oil.
 

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