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Structure of 2153-26-6

Chemical Structure| 2153-26-6

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Product Details of [ 2153-26-6 ]

CAS No. :2153-26-6
Formula : C11H18O2
M.W : 182.26
SMILES Code : O=COC(C)(C1CC=C(CC1)C)C

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Application In Synthesis of [ 2153-26-6 ]

* 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 [ 2153-26-6 ]

[ 2153-26-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 64-18-6 ]
  • [ 98-55-5 ]
  • [ 2153-26-6 ]
  • 2
  • [ 463-73-0 ]
  • [ 98-55-5 ]
  • [ 2153-26-6 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In tetrahydrofuran; mineral oil; at 20℃;Inert atmosphere; General procedure: Example 1 : Synthesis of alpha-terpinyl estersThymol, alpha-<strong>[98-55-5]terpineol</strong> and alpha-terpinyl acetate were purchased as fine chemicals from Sigma Aldrich.Other esters were synthesised by reaction of the alpha-<strong>[98-55-5]terpineol</strong> alcohol with the appropriate acid chloride using a literature method [C Wiles, P Watts, S J Haswell and E Pombo-Villar, Tetrahedron 59, 10173 (2003)]. Alternatively, esters were similarly synthesised starting from a commercial mixture of terpinyl esters, comprising about 70 wt-% of alpha-<strong>[98-55-5]terpineol</strong>, 4 wt-% of beta-<strong>[98-55-5]terpineol</strong> and 26 wt-% of gamma-<strong>[98-55-5]terpineol</strong>.Alpha-<strong>[98-55-5]terpineol</strong> (5 g, 32 mmol) was dissolved in dry THF (40 ml) and to it was added a suspension of sodium hydride (60% dispersion in oil, 1.44g, 36 mmol) in dry THF (20 ml). The mixture was then stirred at room temperature under an atmosphere of argon for 15 minutes before addition of the acid chloride (1 .4 equivalents, 45 mmol) and then stirred at room temperature under argon for 2-3 hours. After this period, the reaction was quenched by dropwise addition of water to the reaction vessel until effervescence ceased. Saturated sodium bicarbonate solution (30 ml) was then added and the aqueous phase was separated and washed with dichloromethane (3 x 50 ml). Organics were then combined, dried using a hydrophobic frit and concentrated to dryness. TLC indicated the presence of impurities so the crude materials were purified by column chromatography, eluting with a gradient of petroleum ether and ethyl acetate (varying from 2 to 10% ethylacetate). Relevant fractions were identified by TLC, combined and concentrated to dryness yielding the desired products whose structures were confirmed by NMR.
  • 3
  • [ 1558-67-4 ]
  • [ 98-55-5 ]
  • [ 2153-26-6 ]
YieldReaction ConditionsOperation in experiment
15.5% With p-toluenesulfonyl chloride; at 20℃; for 1.5h; General procedure: A mixture ofalpha-<strong>[98-55-5]terpineol</strong> (1, 2mmol), acid anhydride (3mL) and TsCl (0.2mmol) was stirred at room temperaturefor 1.5h, and then neutralized to pH7-8 with 10% NaOH aqueous solution, washed with water (2×10mL) and brine (10mL). The organic layer was separated and dried over anhydrous Na2SO4, then concentrated and purified by silica gel column chromatography (petroleum ether/ethyl acetate=1:5 v/v) to afford the desired products.4.1.1.1 28 2-(4-methylcyclohex-3-enyl)propan-2-yl formate (2a) (0016) Colorless oily liquid (15.5%).1H NMR (500MHz, CDCl3)delta 8.04 (s, 1H), 5.36 (s, 1H), 2.05-1.96 (m, 4H), 1.84-1.80 (m, 2H), 1.64 (s, 3H), 1.47 (s, 3H),1.46 (s, 3H) 1.34-1.26 (m, 1H);
3.0032 g With p-toluenesulfonyl chloride; at 20℃; for 8h; In the absence of water,In a round bottom flaskAlpha-<strong>[98-55-5]terpineol</strong>5g,Formic anhydride 20 mL and catalyst (p-Tscl)0.02 g, the magnetic stirring reaction at room temperature,8 hours after the reaction is complete,Stop the reaction.The resulting reaction solution was neutralized with 10% Na0H solution to the excess formic anhydride to pH 7-8.And then extracted twice with water,The third time with saturated salt water extraction,After the organic phase layer was removed with anhydrous sodium sulfate,Spin dry,Add about 6g of silica gel.Take 300 ~ 400 mesh silicone loaded column,After compaction with petroleum ether pressure column three times,Mix the sample with a scraper (try to scratch)Loading. Using petroleum ether as a solution,Pressure chromatography,The chromatographic solution was collected continuously,The tablet determines the purity of the product,Collecting the chromatographic solution,merge,Spin dry.The oil obtained after drying is 3.0032 g of the formate of alpha-<strong>[98-55-5]terpineol</strong>
 

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