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Chemical Structure| 93431-20-0 Chemical Structure| 93431-20-0

Structure of 93431-20-0

Chemical Structure| 93431-20-0

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Product Details of [ 93431-20-0 ]

CAS No. :93431-20-0
Formula : C13H17NO3
M.W : 235.28
SMILES Code : O=C(O)CCCCC1=CC=CC(NC(C)=O)=C1

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Application In Synthesis of [ 93431-20-0 ]

* 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.

  • Upstream synthesis route of [ 93431-20-0 ]

[ 93431-20-0 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 93431-20-0 ]
  • [ 3470-55-1 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: at 0 - 100℃; for 3 h;
Stage #2: at 0 - 35℃;
To mechanically-stirred polyphosphoric acid (2000 g) at 100° C. was added in portions over several min E28B (93.2 g, 396 mmol). The mixture then was stirred at 100° C. for 3 h. At this point external heating was discontinued. While the reaction mixture was still hot water-ice was added in small portions such that the temperature remained at 80-100° C. [Note: this addition is initially very exothermic. External cooling was employed as needed to help keep the temperature in the desired range.]The addition of water-ice was continued until the total reaction volume was 4500 mL. By this time the mixture had cooled to 0-10° C. With external cooling, 50percent aqueous sodium hydroxide solution was added at a rate such that the reaction temperature remained at <35° C. This addition was continued until the aqueous mixture reached pH 3-4. The mixture then was extracted with ethyl acetate. The combined extracts were washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. Column chromatography of the residue on silica gel (elution: 0-5percent diethyl ether/methylene chloride), followed by crystallization of the material from methylene chloride/hexane, provided 58.5 g (84percent) of E28C: NMR (300 MHz, CDCl3) δ 7.69 (d, 1H, J=8.5 Hz), 6.57 (d of d, 1H, J=8.5, 2.2 Hz), 6.47 (d, 1H, J=2.2 Hz), 2.84 (m, 2H), 2.69 (m, 2H), 1.81 (m, 4H).
References: [1] Patent: US2007/249583, 2007, A1, . Location in patent: Page/Page column 77.
[2] Journal of Organic Chemistry, 1962, vol. 27, p. 70 - 76.
 

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