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Method for preparing 2-(6'-methoxy-2'-naphthyl) propenol by allylic oxidation

A methoxy, allyl alcohol technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., to achieve the effects of easy operation, high product yield, and low environmental pollution

Active Publication Date: 2013-01-16
XUZHOU LIFANG MECHANICAL & ELECTRICAL EQUIP MFG CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the present invention, the allyl position of the 2-(6'-methoxy-2'-naphthyl)propene compound is oxidized to prepare allyl alcohol compounds, which has not been reported yet

Method used

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  • Method for preparing 2-(6'-methoxy-2'-naphthyl) propenol by allylic oxidation
  • Method for preparing 2-(6'-methoxy-2'-naphthyl) propenol by allylic oxidation
  • Method for preparing 2-(6'-methoxy-2'-naphthyl) propenol by allylic oxidation

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Preparation of 1,3-bis(N-phenylcarbamoylethyl)imidazolium hexafluorophosphate ionic liquid

[0021]

[0022] Dissolve N-phenyl-3-chloropropionamide (0.2mol) in 30mL of acetonitrile, then add 0.1mol of imidazole, heat to reflux for 24 hours, distill off the acetonitrile, recrystallize ethanol to obtain a white solid, add it to a 500mL beaker , plus 0.22mol of KPF 6 and 200mL of water, stirred and reacted at room temperature for 24h, filtered to obtain a white solid, and recrystallized from ethanol to obtain 1,3-bis(N-phenylcarbamoylethyl)imidazole hexafluorophosphate, with a yield of 47.2%, m.p.171 ~173°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 10.08(s, 2H), 9.21(s, 1H), 7.76(s, 2H), 7.53(d, 4H, J=7.6Hz), 7.27(t, 4H, J=7.6Hz), 7.04( t, 2H, J=7.20Hz), 4.46(t, 4H, J=6.4Hz), 2.95(t, 4H, J=6.0Hz); IR(KBr)v: 3418, 3147, 1692, 1599, 1533, 1444, 1165, 845, 750, 558cm -1 .

Embodiment 2

[0024] Dissolve 0.2 g (1 mmol) of 2-(6'-methoxy-2'-naphthyl)propene in 10 ml of acetone, 1,3-bis(N-phenylcarbamoylethyl)imidazole hexafluoro Phosphate ionic liquid 0.51 g (1 mmol), benzoyl peroxide 0.24 g, heating to 50 ° C, feed weak air into the reaction system and keep stirring for 10 hours, TLC tracking detection until the reaction is complete, after the end of the reaction , extracted with toluene, concentrated, and separated by silica gel column chromatography [V (ethyl acetate) / V (n-hexane) = 1 / 2] to obtain 2-(6'-methoxy-2'-naphthyl) allyl alcohol The product is 0.19 g, and the yield is 89%. Melting point 132~133℃; 1 HNMR (CDCl 3 , 400MHz) δ: 1.76(s, 1H), 3.91(s, 3H), 4.63(s, 2H), 5.41(s, 1H), 5.58(s, 1H), 7.11~7.16(m, 2H), 7.57 ~7.59(m, 1H), 7.70~7.74(m, 2H), 7.82(m, 1H); 13 C NMR (CDCl 3 , 400MHz) δ: 60.1, 65.9, 106.4, 113.1, 119.7, 125.3, 125.5, 127.6, 129.5, 130.4, 134.9, 139.1, 147.8, 158.6; IR (KBr) v: 3050, 1590, 1450, 1390cm -1 ; MS (70eV) m / z (%): 214 (M ...

Embodiment 3

[0026] Dissolve 0.2 g (1 mmol) of 2-(6'-methoxy-2'-naphthyl)propene in 5 ml of acetone, 1,3-bis(N-phenylcarbamoylethyl)imidazole hexafluoro Phosphate ionic liquid 0.51 g (1 mmol), benzoyl peroxide 0.24 g, heating up to 80 ° C, feeding weak air into the reaction system and stirring continuously for 10 hours, TLC tracking detection until the reaction is complete, after the end of the reaction , extracted with toluene, concentrated, and separated by silica gel column chromatography [V (ethyl acetate) / V (n-hexane) = 1 / 2] to obtain 2-(6'-methoxy-2'-naphthyl) allyl alcohol The product is 0.19 g, and the yield is 89%.

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Abstract

The invention discloses a method for preparing 2-(6'-methoxy-2'-naphthyl) propenol with a structure shown as a formula (I) by allylic oxidation. The method comprises the following steps that: 2-(6'-methoxy-2'-naphthyl) propylene with the structure as a formula (II) is used as a raw material, molecular oxygen is used as an oxidant, and 1,3-bis(benzyl carbamyl ethyl-2'-naphthyl) imidazolium hexafluorophosphate ionic liquid shown as a formula (III) / benzoyl peroxide is used as a catalytic system; and methyl on allylic position of the 2-(6'-methoxy-2'-naphthyl) propylene performs oxidation reaction in acetone to prepare the 2-(6'-methoxy-2'-naphthyl) propenol. The preparation method by using the allylic oxidation has the advantages of simple preparation process, easy operation, high product yield, low cost, small environmental pollution and the like through optimization on the oxidant and the catalytic system.

Description

(1) Technical field [0001] The invention relates to a method for preparing 2-(6'-methoxy-2'-naphthyl) allyl alcohol. (2) Background technology [0002] Naproxen (Naproxen) is a non-steroidal anti-inflammatory, antipyretic and analgesic drug, which has a broad demand market at home and abroad. 2-(6'-methoxy-2'-naphthyl)allyl alcohol is an important intermediate of Naproxen medicine. This was studied by Dustin K. James et al. in US Pat. No. 5,286,902. However, in the reported synthetic route, starting from 2-methoxy-6-isopropylnaphthalene, in a high-temperature tubular reactor, after dehydrogenation with a dehydrogenation catalyst to generate an allylnaphthalene compound, after selenium dioxide Made by oxidation. With this synthetic method, the operation is complicated, the reaction conditions are harsh, the selenium dioxide oxidant used is highly toxic, and the source of raw materials for the synthesis of 2-methoxy-6-isopropylnaphthalene is difficult, the synthetic route i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/23C07C41/26
Inventor 裴文孙莉王昭杨培风郑洁张皓雪郭罕奇
Owner XUZHOU LIFANG MECHANICAL & ELECTRICAL EQUIP MFG CO LTD