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[ CAS No. 1462-03-9 ] {[proInfo.proName]}

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Chemical Structure| 1462-03-9
Chemical Structure| 1462-03-9
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Product Details of [ 1462-03-9 ]

CAS No. :1462-03-9 MDL No. :MFCD00001364
Formula : C6H12O Boiling Point : No data available
Linear Structure Formula :C5H8(OH)(CH3) InChI Key :CAKWRXVKWGUISE-UHFFFAOYSA-N
M.W : 100.16 Pubchem ID :73830
Synonyms :

Safety of [ 1462-03-9 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P280-P370+P378-P403-P501 UN#:1325
Hazard Statements:H228 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 1462-03-9 ]

* 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 [ 1462-03-9 ]

[ 1462-03-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 10226-29-6 ]
  • [ 1462-03-9 ]
  • 2
  • [ 1462-03-9 ]
  • 1-methyl-1,4-epoxycyclopentane [ No CAS ]
  • [ 10226-29-6 ]
  • 3
  • [ 1462-03-9 ]
  • [ 10226-29-6 ]
YieldReaction ConditionsOperation in experiment
56% A mixture of 1-methylcyclopentanol (4.00 g, 39.94 mmol) and K2CO3 (33.11 g, 239.6 mmol) in CHCl3 (130 mL) was stirred at 0 C. for 15 min., and then bromine (10.23 mL, 199.7 mmol) was then added. The reaction mixture was stirred at 0 C. for 2.5 hours, then poured slowly into an ice-chilled saturated aqueous Na2S2O3 solution (100 mL). The organic layer was separated, washed with water (2×100 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column (pet ether:EtOAc 3:1) give the desired product 6-bromohexan-2-one as a colorless oil (4 g). Yield 56% (98% purity, UV=214 nm, ESI no found). 1H- NMR (400 MHz, CDCl3) delta 1.66-1.80 (m, 2H), 1.82-1.93 (m, 2H), 2.15 (s, 3H), 2.48 (t, J=7.3 Hz, 2H), 3.41 (t, J=6.5 Hz, 2H)
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of commercially available 1-methylcyclopentanol (4.00 g, 39.94 mmol) in CHCI3 (130 mL) at 0 0C was treated with K2CO3 (33.1 1 g, 239.62 mmol) <n="65"/>and the reaction mixture was stirred for 15 min. Bromine (10.23 ml_, 199.68 mmol) was then added and the reaction mixture was stirred at 0 0C for 2.5 h. The reaction mixture was slowly poured to an ice-chilled sat. aq. Na2S2O3 solution (100 ml_). The org. layer was washed with water (2 x 100 ml_), dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (gradient hept ? 75:25 hept- EA) gave the title compound as a yellow oil: TLC: rf (75:25 hept-EA) = 0.36. 1H NMR (400 MHz, CDCI3) ￡ 1.66-1.80 (m, 2H), 1.82-1.93 (m, 2H), 2.15 (s, 3H), 2.48 (t, J = 7.3 Hz, 2H), 3.41 (t, J = 6.5 Hz, 2H).
6-Bromo-hexan-2-oneIn a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of commercially available 1-methylcyclopentanol (4.00 g, 39.94 mmol) in CHCl3 at 0 C. (2.6 mL) was treated with K2CO3 (33.11 g, 239.62 mmol) and the reaction mixture was stirred for 15 min. Bromine (10.23 mL, 199.68 mmol) was then added and the reaction mixture was stirred at 0 C. for 2.5 h. The reaction mixture was slowly poured onto an ice-chilled sat. aq. Na2S2O3 solution (100 mL). The org. layer was washed with water (2×100 mL), dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (gradient hept?75:25 hept-EA) gave the title compound as a yellow oil. TLC: rf (75:25 hept-EA)=0.36. 1H NMR (400 MHz, CDCl3) delta 1.66-1.80 (m, 2H), 1.82-1.93 (m, 2H), 2.15 (s, 3H), 2.48 (t, J=7.3 Hz, 2H), 3.41 (t, J=6.5 Hz, 2H).
With bromine; potassium carbonate; In chloroform-d1; at 0℃; for 5h; Step A: 6-bromohexan-2-oneTo a solution of l-methylcyclopentanol (7.0 g, 69.9 mmol) in CHCI3 (200 mL) at 0 C was added K2C03 (58.0 g, 419 mmol) and then carefully Br2 (55.8 g, 349 mmol). The mixture was stirred at 0 C for 5 h. The reaction was quenched by slowly adding saturated a2S203 (200 mL) and the mixture was extracted with Et20 (200 mL). Tthe organic layer was washed with water (2x200 mL) and brine (3x200mL), dried over MgS04, and concentrated to afford the title compound: 1H NMR (500 MHz, CDC13) delta 3.43 (m, 2H)S 2.49 (m, 2H), 2.17 (s, 3H), 1.88 (m, 2H), 1.76 (m, 2H).
445 mg With bromine; In dichloromethane; for 6h;Cooling with ice; 1-Methylcyclopentanol (501 mg, 5.0 mmol) was dissolved in dichloromethane (15 ml), and the mixture was stirred for 10 min, and then bromine (3.995 g, 25.0 mmol) was slowly added and stirred for 6 h under ice bath. After the reaction, the solution was slowly added with saturated sodium thiosulfate solution (20 ml), and then extracted with diethyl ether, water and brine, dried over anhydrous sodium sulfate, filtered and evaporated to dryness. 6-Bromo-2-hexanone (445 mg, 2.49 mmol).

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