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Method for synthesis of phenylacetic acid by carbonylation of benzyl chloride

A benzyl chlorocarbonyl compound synthesis technology, applied in chemical instruments and methods, carbon monoxide reaction to prepare carboxylic acid, organic compound/hydride/coordination complex catalyst, etc., can solve the problem of complex catalyst preparation, limitation of phenylacetic acid promotion, and difficult Long-term storage and other issues, to achieve excellent catalytic activity, easy treatment and purification, and easy operation

Inactive Publication Date: 2015-02-18
NORTHWEST UNIV +1
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Problems solved by technology

Among them, Pd and Rh are expensive, which limits their impetus to the industrial production of phenylacetic acid
Co catalysts have been extensively studied due to their low cost, and the most common ones are Co 2 (CO) 8 , but the preparation of the catalyst is complicated and it is not easy to store for a long time

Method used

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  • Method for synthesis of phenylacetic acid by carbonylation of benzyl chloride
  • Method for synthesis of phenylacetic acid by carbonylation of benzyl chloride
  • Method for synthesis of phenylacetic acid by carbonylation of benzyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Synthesis of 2-(4-amino-2-phenylhydroxy)benzimidazole

[0021] Add 0.12 mol of o-phenylenediamine, 0.1 mol of p-aminosalicylic acid and 100.0 ml of polyphosphoric acid into a 150 ml round bottom flask, and react with mechanical stirring at 190°C for 4 hours. After the reaction is over, cool the reaction solution to 100°C and pour it into ice water. After filtering, washing and recrystallizing the precipitated precipitate, the obtained yellow powder is 2-(4-amino-2-phenylhydroxy)benzimidazole. The yield was 86%.

[0022] 2-(4-Amino-2-phenylhydroxy)benzimidazole C 13 h 11 N 3 O: m.p. 243–244 ° C (lit. 241–242 ° C). 1 H NMR (DMSO- d 6 , 400 MHz), δ (ppm): 12.98 (s, 1H, OH), 12.67 (s, 1H, NH), 7.66 (d, J = 8.5 Hz, 1H), 7.52 (s, 2H), 7.18 (dd, J = 5.7, 3.0 Hz, 2H), 6.21 (d, J = 8.5 Hz, 1H), 6.14 (s, 1H), 5.67 (s, 2H, NH 2 ).IR (KBr), ν (cm -1 ): 3437, 3353, 3331, 3235, 1637, 1591, 1484, 1412, 1268, 964, 899, 842, 805, 745. MS m / z (%): 226 ...

Embodiment 2

[0023] Embodiment 2: the synthesis of transition metal complex

[0024] In a 25ml round bottom flask, add 0.5 mmol CoCl 2 ·6H 2 O. 1.2 mmol 2-(4-amino-2-phenylhydroxy)benzimidazole, 10 ml methanol as solvent, stir at room temperature for 4-5 hours, a maroon precipitate forms, filter, wash the solid with a small amount of methanol, and let it dry naturally at room temperature Dry.

[0025] IR (KBr), ν (cm -1 ): 3418, 1618, 1494, 1393, 1262, 1131, 817, 743, 617, 519, 466 cm -1 ; Elemental analysis (theoretical): C: 62.18 (61.54), H: 3.07 (3.97), N: 15.91 (16.56).

[0026] The synthesis method of Cu and Zn metal complexes is similar to the above-mentioned method, and a suitable single crystal is cultivated through recrystallization, and the structure is as follows: figure 1 and 2 shown.

[0027] 2-(4-Amino-2-phenylhydroxy)benzimidazole copper complex Cu(C 13 h 10 N 3 O) 2 : IR (KBr), ν (cm -1 ): 3375, 3000, 1610, 1500, 1440, 1250, 1125, 930, 745, 513, 470. Elemen...

Embodiment 3

[0029] Embodiment 3: the synthesis of catalytic promoter benzimidazole Schiff base

[0030] In a 50 ml round bottom flask, add 2.5 mmol 2,4-dichlorobenzaldehyde, 2 mmol 2-(4-amino-2-phenylhydroxy)benzimidazole and 10.0 ml anhydrous methanol, stir and reflux at 65 °C 4h. After the reaction solution was cooled and left to stand, light yellow powder precipitated out. After filtration, washing and recrystallization, the Schiff base was obtained with a yield of 73%.

[0031] The Schiff base C obtained above 20 h 13 Cl 2 N 3 O: m.p. 300–301 ° c. 1 H NMR (DMSO- d 6, 400 MHz), δ (ppm):13.33 (s, 2H), 8.99 (s, 1H), 8.20 (d, J = 10.5 Hz, 2H), 7.82 (s, 1H), 7.69 (s, 2H), 7.60 (d, J = 7.8 Hz, 1H), 7.30 (dd, J = 5.4, 2.8 Hz, 3H), 7.12 (d, J = 8.7 Hz, 1H). IR (KBr), ν (cm -1 ): 3321, 3059, 1583, 1495, 1387, 1262, 1132, 869, 811, 744. MS: m / z (%): 382 (M+1). Anal. calcd. for C 20 h 13 Cl 2 N 3 O: C 62.18, H 3.13, N 10.13; Found: C 62.84, H 3.43, N 10.99.

[0032]...

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Abstract

The invention discloses a method for synthesis of phenylacetic acid by carbonylation of benzyl chloride. The key technology includes that: a 2-(4-amino-2-hydroxyphenyl)benzimidazole metal complex as shown in the structural formula (I) is used as a main catalyst in the reaction process, M is Co2+, Cu2+, and Zn2+, and benzimidazole Schiff base is used as a catalytic additive. The catalytic system is simple in synthesis process, has excellent catalytic activity for carbonylation of benzyl chloride, and is small in usage amount, easy to operate, low in cost, and easy for product postprocessing purification. Reaction conditions are mild and easy to achieve, and the reaction temperature is only 60-70 DEG C.

Description

technical field [0001] The invention relates to a method for synthesizing phenylacetic acid by carbonylation of benzyl chloride, which belongs to the technical field of organic chemistry. Background technique [0002] As an important intermediate, phenylacetic acid is widely used in medicine, pesticides, and spices, and is an important synthetic raw material for the drug penicillin. Phenylacetic acid is a fungicide and plant growth agent commonly found in natural products such as strawberries, grapes, cocoa, honey, and green tea. With the continuous development of medicine, agriculture and fragrance industry, the market demand is also increasing due to its wide range of uses. There are dozens of synthesis methods of phenylacetic acid, mainly sodium cyanide method, phenylacetamide hydrolysis method, benzene method, electrochemical method and benzyl chlorocarbonylation method. Among them, the sodium cyanide method is the main domestic industrial production method. Although t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C57/32C07C51/10B01J31/22
Inventor 王淑莉李剑利师艳宁金洗郎史真
Owner NORTHWEST UNIV
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