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[ CAS No. 152775-45-6 ]

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Chemical Structure| 152775-45-6
Chemical Structure| 152775-45-6
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CAS No. :152775-45-6 MDL No. :MFCD03428544
Formula : C10H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :161.20 g/mol Pubchem ID :14981817
Synonyms :

Safety of [ 152775-45-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 152775-45-6 ]

  • Upstream synthesis route of [ 152775-45-6 ]
  • Downstream synthetic route of [ 152775-45-6 ]

[ 152775-45-6 ] Synthesis Path-Upstream   1~6

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YieldReaction ConditionsOperation in experiment
99%
Stage #1: With sodium hydroxide In ethanol at 120℃; pressure reactor
Stage #2: With hydrogenchloride In water
Preparation 1664-Methoxy-3,5-dimethylbenzoic acidTo a suspension of 4-methoxy-3,5-dimethylbenzonitrile in ethanol (32 mL) 8M NaOH (163 mL) was added and mixture stirred at 120°C overnight in a pressure reactor. Ethanol was removed, water was added and solution was washed with diethyl ether. Then aquous layer was acidified with concentrated HCI and product extracted with ethyl acetate, organic layer was washed with water and brine, dried over magnesium sulphate, filtered and concentrated to yield the title compound as a white solid (99percent yield).LRMS: m/z 181 (M+1 )+ Retention time: 5.52 min (Method B)
99%
Stage #1: With water; sodium hydroxide In ethanol at 120℃;
Stage #2: With hydrogenchloride In water
To a suspension of 4-methoxy-3,5-dimethylbenzonitrile in ethanol (32 mL) 8M NaOH (163 mL) was added and mixture stirred at 120°C overnight in a pressure reactor. Ethanol was removed, water was added and solution was washed with diethyl ether. Then aquous layer was acidified with concentrated HCl and product extracted with ethyl acetate, organic layer was washed with water and brine, dried over magnesium sulphate, filtered and concentrated to yield the title compound as a white solid (99percent yield). LRMS: m/z 181 (M+1)+ Retention time: 5.52 min (Method B)
Reference: [1] Patent: WO2011/144338, 2011, A1, . Location in patent: Page/Page column 92
[2] Patent: EP2390252, 2011, A1, . Location in patent: Paragraph 0449; 0450
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Reference: [1] Organic Letters, 2015, vol. 17, # 11, p. 2602 - 2605
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  • [ 14804-38-7 ]
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YieldReaction ConditionsOperation in experiment
97% at 136℃; 5-Bromo-2-methoxy-l,3-dimethylbenzene (294 mL, 1841.12 mmol) and copper(I) cyanide (196 g, 2189.09 mmol) were added to N,N-dimethylformamide (1700 mL) and the resulting mixture heated at 136 0C overnight. The mixture was allowed to attain r.t. and then poured into a solution of ammonia (25percent in water, 1 L) and water (1 L). Toluene (2 L) was added and the mixture was stirred for 20 min, then the organic phase was separated, filtered and concentrated. The residue was purified by gradient column chromatography over silica, eluting with 0-50percent ethylacetate in heptanes. The desired fractions were evaporated to give the title compound (289 g, 97percent yield): 1H-NMR (500 MHz, CDCl3) δ 2.43 (s, 7 H), 3.89 (s, 3 H), 7.46 (s, 2 H); MS (CI+) m/z 162 [M+ 1]+.
Reference: [1] Patent: WO2011/2407, 2011, A1, . Location in patent: Page/Page column 74-75
[2] Journal of Organic Chemistry, 2010, vol. 75, # 16, p. 5643 - 5660
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  • [ 74-88-4 ]
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 22, p. 3240 - 3250
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  • [ 14804-38-7 ]
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Reference: [1] Organic Letters, 2008, vol. 10, # 23, p. 5429 - 5432
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  • [ 1004-66-6 ]
  • [ 75-05-8 ]
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Reference: [1] Organic Letters, 2015, vol. 17, # 11, p. 2602 - 2605
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