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Chemical Structure| 74998-19-9

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Product Details of [ 74998-19-9 ]

CAS No. :74998-19-9
Formula : C11H12O3
M.W : 192.21
SMILES Code : O=C(OC)C1=CC=CC(CC(C)=O)=C1
MDL No. :MFCD02258776
InChI Key :FRHNAXWWCGBMIE-UHFFFAOYSA-N
Pubchem ID :20134188

Safety of [ 74998-19-9 ]

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 [ 74998-19-9 ]

* 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 [ 74998-19-9 ]

[ 74998-19-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 108-22-5 ]
  • [ 618-89-3 ]
  • [ 74998-19-9 ]
YieldReaction ConditionsOperation in experiment
Preparation 65: methyl [3-(2-oxopropyl)phenyl]acetate Tributyltin methoxide (80.3ml, 279mmol), <strong>[618-89-3]methyl 3-bromobenzoate</strong> (53.5g, 249mmol), isopropenyl acetate (39.4ml, 358mmol), palladium(II)acetate (2.6g, 11.6mmol) and tri-o -tolylphosphine (7.1 g, 23.2mmol) were stirred together in toluene (350ml) at 100C under nitrogen for 18 hours. After cooling, the reaction was treated with 4M aqueous potassium fluoride solution (560ml) and stirred for 2 hours. The resulting mixture was diluted with further toluene (200ml) and filtered through celite, washing the filter pad with ethyl acetate. The organic phase was separated, dried (sodium sulfate) and reduced in vacuo. The residue was purified by flash column chromatography on silica gel eluding with ethylacetate:pentane (10:90, changing to 20:80, by volume) to give the title compound (45.3g) as an orange oil. 1H NMR (400MHz, CDCl3): δ = 7.95-7.93 (1H, d), 7.87 (1H, s), 7.43-7.37 (2H, m), 3.91 (3H, s), 3.75 (2H, s), 2.18 (3H, s) ppm. LRMS (electrospray): m/z [M+Na]+ 215, [M-H]- 191.
Tributyltin methoxide (80.3 mL, 279 mmol), <strong>[618-89-3]methyl 3-bromobenzoate</strong> (53.5 g, 249 mmol), isopropenyl acetate (39.4 ml, 358 mmol), palladium (11) acetate (2.6 g, 11.6 mmol) and tri-ortho-tolylphosphine (7.1 g, 23.2 mmol) were stirred together in toluene (350 mL) at 100 C under nitrogen for 18 hours. After cooling, the reaction was treated with potassium fluoride solution (4M, 560 ml) and stirred for 2 hours. The resulting mixture was diluted with further toluene (200 mL) and filtered through Celite No., washing the filter pad with ethyl acetate. The organic phase was separated, dried (sodium sulfate) and reduced in vacuo. The residue was purified by chromatography eluting with ethylacetate : pentane 10 : 90 to 20: 80 to give the title compound (45.3 g) as an orange oil- 'H NMR-(400MHz, CDCI3) ã : 2.18 (3H, s), 3.75 (2H, s), 3.91 (3H, s), 7.43-7. 37 (2H, m), 7.87 (1H, s), 7.95-7. 93 (1H, d); LRMS ESI m/z 215 [M+Na] +, 191 [M- H]-.
Tributyltin methoxide (80.3 ml, 279 mmol), <strong>[618-89-3]methyl 3-bromobenzoate</strong> (53.5 g, 249 mmol), isopropenyl acetate (39.4 ml, 358 mmol), palladium(II)acetate (2.6 g, 11.6 mmol) and tri-o-tolylphosphine (7.1 g, 23.2 mmol) were stirred together in toluene (350 ml) at 100 C. under nitrogen for 18 hours. After cooling, the reaction was treated with 4M aqueous potassium fluoride solution (560 ml) and stirred for 2 hours. The resulting mixture was diluted with further toluene (200 ml) and filtered through celite, washing the filter pad with ethyl acetate. The organic phase was separated, dried (sodium sulfate) and reduced in vacuo. The residue was purified by flash column chromatography on silica gel eluting with ethylacetate:pentane (10:90, changing to 20:80, by volume) to give the title compound (45.3 g) as an orange oil. 1H NMR (400 MHz, CDCl3): δ=7.95-7.93 (1H, d), 7.87 (1H, s), 7.43-7.37 (2H, m), 3.91 (3H, s), 3.75 (2H, s), 2.18 (3H, s) ppm. LRMS (electrospray): m/z [M+Na]+215, [M-H]-191.
Tributyltin methoxide (80.3ml, 279mmol), <strong>[618-89-3]methyl 3-bromobenzoate</strong> (53.5g, 249mmol), isopropenyl acetate (39.4ml, 358mmol), palladium(ll)acetate (2.6g, 11.6mmol) and tri-o-tolylphosphine (7.1g, 23.2mmol) were stirred together in toluene (350ml) at 100C under nitrogen for 18 hours. After cooling, the reaction was treated with 4M aqueous potassium fluoride solution (560ml) and stirred for 2 hours. The resulting mixture was diluted with further toluene (200ml) and filtered through Celite, washing the filter pad with ethyl acetate. The organic phase was separated, dried (sodium sulfate) and reduced invacua. The residue was purified by flash column chromatography on silica gel eluting with ethylacetate:pentane (10:90, changing to 20:80, by volume) to give the title compound (45.3g) as an orange oil.1H NMR (400MHz, CDCI3): 8 = 7.95-7.93 (1H, d), 7.87 (1H, s), 7.43-7.37 (2H, m), 3.91 (3H, s), 3.75 (2H, s), 2.18 (3H, s) ppm.LRMS (electrospray): m/z [M+Na]+ 215, [M-H]' 191.

 

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