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Chemical Structure| 226555-35-7 Chemical Structure| 226555-35-7

Structure of 226555-35-7

Chemical Structure| 226555-35-7

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Product Details of [ 226555-35-7 ]

CAS No. :226555-35-7
Formula : C10H13FO2
M.W : 184.21
SMILES Code : CCOC1=C(F)C=CC=C1OCC
MDL No. :MFCD15146834
InChI Key :CDXFDHFMNGZBGA-UHFFFAOYSA-N
Pubchem ID :22460126

Safety of [ 226555-35-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 226555-35-7 ]

* 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 [ 226555-35-7 ]

[ 226555-35-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 363-52-0 ]
  • [ 75-03-6 ]
  • [ 226555-35-7 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; After dissolving <strong>[363-52-0]3-fluorocatechol</strong> (1200 g) in dimethylformamide (2500 ml) while cooling on ice, potassium carbonate (540 g) was added, after which ethyl iodide was gradually added. The reaction mixture was stirred at room temperature overnight, an ether-hexane solution was added, the mixture was washed with water and brine and the organic layer was dried over anhydrous magnesium sulfate. The solvent of the organic layer was distilled off under reduced pressure and then the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (269 g) as a yellow oil.1H-NMR(CDCl3)delta(ppm) 1.35(3H,t,J=7.0Hz), 1.43(3H,t,J=7.0Hz), 4.07(2H,q,J=7.0Hz), 4.12(2H,q,J=7.0Hz), 6.65-6.95(3H,m).
  • 2
  • [ 226555-35-7 ]
  • [ 474554-34-2 ]
YieldReaction ConditionsOperation in experiment
With bromine; sodium acetate; In acetic acid; at 0 - 70℃; for 14.0h; After dissolving the 1,2-diethoxy-3-fluorobenzene (269 g) in acetic acid (2000 ml), sodium acetate (294.5 g) was added. A solution of bromine (178 ml) in 150 ml of acetic acid was gradually added thereto dropwise while cooling on ice. After stirring overnight at room temperature, the mixture was stirred at 70C for 14 hours. The reaction mixture was poured into ice water, potassium carbonate was added to adjust the pH to 7, and extraction was performed with ether. The organic layer was dried over anhydrous magnesium sulfate to yield the title compound (480 g) as a brown oil.1H-NMR(CDCl3)δ(ppm) 1.35(3H,t,J=7.0Hz), 1.43(3H,t,J=7.0Hz), 4.04(2H,q,J=7.0Hz), 4.11(2H,q,J=7.0Hz), 6.98(1H,s).
  • 3
  • [ 74-96-4 ]
  • [ 363-52-0 ]
  • [ 226555-35-7 ]
YieldReaction ConditionsOperation in experiment
81% With sodium hydroxide; In ethanol; at 10℃; for 5h;Heating / reflux;Product distribution / selectivity; 2) Synthesis of 1,2-diethoxy-3-fluorobenzene [G1] To a 500 ml flask were added 38.4 (0.3 mol) of <strong>[363-52-0]3-fluorocatechol</strong> [H], 12 g (0.3 mol) of sodium hydroxide and 100 ml of ethanol. After cooling to around 10°C, 100 ml of an ethanol solution of 76.3 g (0.7 mol) of bromoethane was slowly added. After the termination of the addition, they were reacted under a reflux temperature for 5 hours. After the termination of the reaction, dichloromethane was added, followed by extraction. The extraction liquid was washed with water and dried, and the solvent was removed by distillation to obtain 45.5 g of 1,2-diethoxy-3-fluorobenzene [G1] as an oily product. The process yield was 81percent.
81% With sodium hydroxide; In ethanol; at 10℃;Reflux; 2) Synthesis of 1,2-diethoxy-3-fluorobenzene [G1]; To a 500 ml flask were added 38.4 (0.3 mol) of <strong>[363-52-0]3-fluorocatechol</strong> [H], 12 g (0.3 mol) of sodium hydroxide and 100 ml of ethanol. After cooling to around 10° C., 100 ml of an ethanol solution of 76.3 g (0.7 mol) of bromoethane was slowly added. After the termination of the addition, they were reacted under a reflux temperature for 5 hours. After the termination of the reaction, dichloromethane was added, followed by extraction. The extraction liquid was washed with water and dried, and the solvent was removed by distillation to obtain 45.5 g of 1,2-diethoxy-3-fluorobenzene [G1] as an oily product. The process yield was 81percent.
  • 4
  • [ 64-67-5 ]
  • [ 363-52-0 ]
  • [ 226555-35-7 ]
YieldReaction ConditionsOperation in experiment
53% With tetrabutylammomium bromide; potassium carbonate; In tert-butyl methyl ether; for 3.75h;Reflux; To a 3-fluoro-2-hydroxyacetophenone (5, 100 g, 0.648 moles) was add 1N aq. NaOH solution (1.25 Lit., 1.5 equiv.) in a drop-wise manner at 25oC for 30 min. Exotherm upto 40oC was observed. The reaction mixture was further stirred at 40?45oC for 1 h and then cooled to 25°C. 3percent Aq. H2O2 solution was added drop-wise (1.5 Lit., 1.6equiv.) for the period of 1 h, where exotherm upto 50?55°C was observed. The reaction mixtures was further stirred at 25°C for 3 h and then cooled to 10oC. Conc. hydrochloric acid (90 ml) was added with vigorous stirring to bring the pH upto 1.5?2.0 and continued the stirring for 30 min. The reaction mixture was then extracted with tert-butyl methyl ether (1x700 ml, 3x300 ml) and the combined organic layer was evaporated upto 75 percent recovery of MTBE. To the obtained residual organic layer, K2CO3 (294.8 g, 3.3equiv.) and TBAB (20.8 g, 0.064 mol) was added. The reaction mixture was stirred vigorously and diethyl sulfate (328.8 g, 3.3 equiv.) was added drop-wise over 45 min. The mixture was refluxed for 3 h (monitored by GC) and then distilled the MTBE. After cooling the reaction mixture to 40oC, water was added (330 ml) and again heated at 70oC for 2 h for hydrolysis of excess diethyl sulfate (monitored by GC). The reaction mixture was cooled to room temperature and organic layer was separated. The aqueous layer was extracted by tert-butyl methyl ether (2x200 ml). The combined organic layer was evaporated under vacuum to furnish liquid residue of 2 (109.3 g). This residue was subjected for the treatment of sodium borohydride (0.7 g) in 220 ml methanol at rt for 30 min to reduce the respective alkylated acetophenones 4 and 5. The organic layer was concentrated under vacuum and then resulting residue was distilled under vacuum using Micro-Liquid divider. The pure fraction of 2 (62.9 g, 52.6 percent yield, GC purity 99.25 percent) was isolated at 95?99oC and 9 ? 10 mbar. 1HNMR (CDCl3, 300 MHz) delta: 6.97-6.89 (m, 1H, ArH), 6.74-6.65 (m, 2H, ArH), 4.10 (m, 4H, CH2), 1.44 (t, 3H, CH3), 1.37 (t, 3H, CH3). Observed LCMS (M+23) 207.00.
 

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