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Product Details of [ 24078-24-8 ]

CAS No. :24078-24-8 MDL No. :MFCD20923636
Formula : C10H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :BNDZGHTWTJZPSE-UHFFFAOYSA-N
M.W : 178.18 Pubchem ID :20134185
Synonyms :

Safety of [ 24078-24-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338-P304+P340-P405-P501 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 24078-24-8 ]

* 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 [ 24078-24-8 ]

[ 24078-24-8 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 24078-24-8 ]
  • [ 103068-41-3 ]
  • [ 952053-73-5 ]
  • 2
  • [ 5471-81-8 ]
  • [ 68-12-2 ]
  • [ 24078-24-8 ]
YieldReaction ConditionsOperation in experiment
80% A solution of <strong>[5471-81-8]methyl 4-iodo-3-methylbenzoate</strong> (21.7 mmol, 6 g) in dry THF (120 mL) was purged with argon. The solution was cooled to -15C, i-PrMgCl (2M in THF, 108.5 mmol, 54.25 mL), and DMF (130.2 mmol, 10 mL) were added and the reaction was stirred for 2h at -15C and then warmed to 25C and allowed to react for an additional hour. The reaction was quenched with aqueous 1N HCl and extracted with EtAcO. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude was purified by flash chromatography on silica gel using an elution of 6% ethylacetate in hexanes to give methyl 4-formyl-3-methylbenzoate (3.08 g. Yield: 80%). [0092] 1H NMR (400 MHz, CDCl3) delta 10.35 (1H, s), 8.00 (1H, d, J=8Hz), 7.99 (1H, s), 7.86 (1H, d, J=8Hz), 3.95 (3H, s), 2.72 (3H, s) [0093] LC-MS: tR = 2.85 [M+H]+ = not ion. (method 3)
80% With isopropylmagnesium chloride; In tetrahydrofuran; at -15 - 20℃; for 1h;Inert atmosphere; A solution of <strong>[5471-81-8]methyl 4-iodo-3-methylbenzoate</strong> (21 .7 mmol, 6 g) in dry THF (120 mL) was purged with argon. The solution was cooled to -155C, /-PrMgCI (2M in THF, 108.5 mmol, 54.25 mL), and DMF (130.2 mmol, 10 mL) were added and the reaction was stirred for 2h at -155C and then warmed to 255C and allowed to react for an additional hour. The reaction was quenched with aqueous 1 N HCI and extracted with EtAcO. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude was purified by flash chromatography on silica gel using an elution of 6% ethylacetate in hexanes to give methyl 4-formyl-3-methylbenzoate (3.08 g. Yield: 80%). 1 H NMR (400 MHz, CDCI3) delta 10.35 (1 H, s), 8.00 (1 H, d, J=8Hz), 7.99 (1 H, s), 7.86 (1 H, d, J=8Hz), 3.95 (3H, s), 2.72 (3H, s) LC-MS: tR = 2.85 [M+H]+ = not ion. (method 3)
80% With isopropylmagnesium chloride; In tetrahydrofuran; at -15 - 25℃; for 3h;Inert atmosphere; A solution of <strong>[5471-81-8]methyl 4-iodo-3-methylbenzoate</strong> (21 .7 mmol, 6 g) in dry THF (120 mL) was purged with argon. The solution was cooled to -155C, /-PrMgCI (2M in THF, 108.5 mmol, 54.25 mL), and DMF (130.2 mmol, 10 mL) were added and the reaction was stirred for 2 h at -155C and then warmed to 255C and allowed to react for an additional hour. The reaction was quenched with aqueous 1 N HCI and extracted with EtAcO. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude was purified by flash chromatography on silica gel using an elution of 6% ethylacetate in hexanes to give methyl 4-formyl-3-methylbenzoate (3.08g .Yield: 80%). 1 H NMR (400 MHz, CDCI3) delta 10.35 (1 H, s), 8.00 (1 H, d, J=8Hz), 7.99 (1 H, s), 7.86 (1 H, d, J=8Hz), 3.95 (3H, s), 2.72 (3H, s) LC-MS: tR = 2.85 [M+H]+ = not ion (method 3).
80% With isopropylmagnesium chloride; In tetrahydrofuran; at -15 - 25℃; for 3h; full text is not avalable from article
70% With isopropylmagnesium chloride; In tetrahydrofuran; at -15℃; for 2h; Methyl 4-formyl-3-methylbenzoate (1616-18a). To a solution of methyl 4-iodo-3- methylbenzoate (1.0 g, 3.6 mmol) in THF (24 mL, 0.15 M) at -15C was added isopropylmagnesium chloride (7.2 ml, 14.5 mmol, 4.0 equiv). The reaction mixture was allowed to continue stirring at -15C for 2 hrs before N,N-dimethylformamide (1.4 ml, 18mmol, 5.0 equiv) was added. The mixture was warmed to room temperature over a period of 1 hr. At this time the reaction was quenched with HC1 and extracted with EtOAc (3x). The combined organic layers were washed with brine and dried over MgSO4, filtered and concentrated in vacuo.Purification was achieved using flash column chromatography on Si02 (Hexanes/EtOAc:6/1) to yield a white solid (0.45 g, 70 %) which was taken on without further purification.
70% To a stirred solution of 18-2B (3.2 g, 11.5 mmol; TCI) in THF was treated with isopropyl magnesium chloride (/-PrMgCl) in THF (22.8 mL of 2.0 M in THF, 46 mmol) at -15 C. After 2 hr stirring at the same temperature, dry DMF (4.3 mL, 57.5 mmol) was added and the reaction was allowed to warm to 23 C over 1 hr. After consumption of the starting material (by TLC), the reaction was quenched with aqueous 1M HC1 (60 mL), followed by extracted with EtOAc, dried over Na2S04 and concentrated. The crude compound was purified by flash column chromatography (100-200 silica) using 5% EtOAc in hexanes to afford 18-3B (1.4 g, 7.8 mmol, 70% yield) as an off-white solid. MS (ESI): m z 179.2 (M+l)+.

  • 3
  • [ 110-87-2 ]
  • [ 24078-24-8 ]
  • [ 22236-10-8 ]
  • rac-methyl 4-((4aR,5S,10bR)-9-(difluoromethoxy)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl)-3-methylbenzoate [ No CAS ]
  • rac-methyl 4-((4aR,5R,10bR)-9-(difluoromethoxy)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl)-3-methylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With trifluoroacetic acid; In acetonitrile; at 20℃; for 16h; General procedure: Method 2: In order to increase the reaction ratio ofexo isomer a solution of methyl 4-formyl-3-methylbenzoate6 (5.61 mmol, 1 g) in anhydrous ACN(60 mL), p-toluidine (5.1 mmol, 547 mg), 3,4-dihydro-2H-pyran (10.2 mmol, 0.93 mL) and TFA(1.12 mmol, 0.087mL) were added. The reactionmixture was stirred 16 h at RT. Solvent was evaporatedand purification of the crude material (60:40 mixtureof exo/endo diastereomers) by flash chromatographyover silica gel using an elution of 15% ethyl acetate inhexanes afforded 1 g (Yield 50%) of the title exoisomer(exo-1c) and 290 mg (Yield 14%) of the titleendo-isomer (endo-1c).
  • 4
  • [ 110-87-2 ]
  • [ 24078-24-8 ]
  • [ 3158-71-2 ]
  • rac-methyl 4-((4aR,5S,10bR)-9-cyclopropyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl)-3-methylbenzoate [ No CAS ]
  • rac-methyl 4-((4aR,5R,10bR)-9-cyclopropyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl)-3-methylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With trifluoroacetic acid In acetonitrile at 20℃; for 16h; diastereoselective reaction; General procedure for Povarov Reaction General procedure: Method 2: In order to increase the reaction ratio ofexo isomer a solution of methyl 4-formyl-3-methylbenzoate6 (5.61 mmol, 1 g) in anhydrous ACN(60 mL), p-toluidine (5.1 mmol, 547 mg), 3,4-dihydro-2H-pyran (10.2 mmol, 0.93 mL) and TFA(1.12 mmol, 0.087mL) were added. The reactionmixture was stirred 16 h at RT. Solvent was evaporatedand purification of the crude material (60:40 mixtureof exo/endo diastereomers) by flash chromatographyover silica gel using an elution of 15% ethyl acetate inhexanes afforded 1 g (Yield 50%) of the title exoisomer(exo-1c) and 290 mg (Yield 14%) of the titleendo-isomer (endo-1c).
  • 5
  • [ 24078-24-8 ]
  • [ 17768-41-1 ]
  • methyl 4-((((adamantan-1-yl)methyl)amino)methyl)-3-methylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71.3% A solution ofmethyl3-methyl-4-formylbenzoate (100 mg, 0.561 moll.O eq.) and<strong>[17768-41-1]1-adamantanemethylamine</strong> (1 00 mg, 0. 606 mol, 1.1 eq.) in 2 mL methanol was stirred for2 hat room temperature. Next, 50 mg sodium borohydride was added and the reactionmixture was stirred until no starting material remained. The mixture was concentrated invacuo, partitioned between ethyl acetate and water, the aqueous layer extracted two more times with ethyl acetate and the combined organic phases were dried over sodium sulfate.The solvent was removed under reduced pressure and the product was purified by columnchromatography. The title product (131 mg, 0.400 mmol, 71.3%) was obtained as a clearoil that solidified upon standing. 1H NMR (500 MHz, Chloroform-d) 8 7.91 -7.78 (m,2H), 7.42 (d, J = 7.8 Hz, 1H), 3.91 (d, J = 1.2 Hz, 3H), 3.79 (s, 2H), 2.38 (s, 3H), 2.29 (d,J = 1.4 Hz, 2H), 1.98 (s, 3H), 1.80- 1.49 (m, 12H).
  • 6
  • [ 5157-08-4 ]
  • [ 24078-24-8 ]
  • 3-methyl-4-[(6-methyl-3-oxo-2,3-dihydropyridazin-4-yl)methyl]benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
6.98 g With potassium hydroxide; In ethanol; at 70℃; for 1h; A mixture of 4,5-dihydro-6-methyl-3(2H)pyridazinone (8.35 g), methyl 4-formyl-3-methylbenzoate (13.27 g) and a solution of potassium hydroxide (12.54 g) in ethanol (446 mL) was stirred at 70C for 1 hour. The reaction mixture was acidified with hydrochloric acid (1 mol/L) under ice-cooling. The mixture was stirred under ice-cooling for 30 minutes, and then the precipitated solid was collected by filtration to give the title compound (6.98 g). MS (ESI_APCI, m/z): 259 (M+H)+
  • 7
  • [ 67-56-1 ]
  • [ 24078-23-7 ]
  • [ 24078-24-8 ]
YieldReaction ConditionsOperation in experiment
52% With thionyl chloride at 0 - 30℃; for 10h; 7.1 Step 1: To a solution of 4-formyl-3-methyl-benzoic acid (900 mg, 5.48 mmol) in MeOH (10 mL) was added SOCh (0.8 mL, 11.0 mmol) dropwise at 0 °C. The mixture was stirred at 30 °C for 10 h. The mixture was concentrated, and the residue was purified by column chromatography to obtain methyl 4-formyl-3-methylbenzoate (510 mg, 52%) as a white solid. NMR (400MHz, CDCh) 10.35 (s, 1H), 8.00 (d, J = 7.9 Hz, 1H), 7.95 (s, 1H), 7.87 (d, J = 7.9 Hz, 1H), 3.96 (s, 3H), 2.72 (s, 3H).
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