Preparation method of 2-methyl-3-biphenylmethanol

A technology of phenyl benzyl alcohol and methyl benzoic acid is applied in the field of preparation of 2-methyl-3-phenyl benzyl alcohol, can solve the problems of harsh reaction conditions, low yield, many side reactions, etc., and achieves the reaction yield. The effect of high rate and simple process

Inactive Publication Date: 2012-07-25
NUTRICHEM LAB CO LTD
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0006] In the preparation process of the above-mentioned 2-methyl-3-phenylbenzyl alcohol, the synthesis of biphenyl groups usually adopts reaction routes such as Ulmann, Wurtz, Grignard, but these synthetic routes have harsh reaction conditions, many side reactions and low yields. Lower problems

Method used

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  • Preparation method of 2-methyl-3-biphenylmethanol
  • Preparation method of 2-methyl-3-biphenylmethanol

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Add 3-bromo-2-methylbenzoic acid (4.9g, 22.4mmol), palladium acetate (55mg, 0.23mmol), sodium carbonate (7.2g, 68.1mmol) to the 500mL reaction flask under nitrogen protection (reaction system pH 8-9), phenylboronic acid (3.1 g, 25 mmol) and water (125 mL). The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into 2N hydrochloric acid, the product was extracted with ethyl acetate (3×150 mL), the organic layers were combined, dried and concentrated to give the title compound (90% yield).

Embodiment 2

[0032] Add 3-bromo-2-methylbenzoic acid (4.9g, 22.4mmol), 5% palladium / carbon (1.12mmol), potassium carbonate (6.2g, 44.8mmol) to the 500mL reaction flask under nitrogen protection (reaction system pH 8-9), phenylboronic acid (3.1 g, 25 mmol) and a mixture of N,N-dimethylacetamide and water (20 / 1 (v / v), 125 mL). The reaction mixture was stirred at 80 °C for 1 hour. The reaction mixture was poured into 2N hydrochloric acid, the product was extracted with ethyl acetate (3×150 mL), the organic layers were combined, dried and concentrated to give the title compound (94% yield).

Embodiment 3

[0034] Add 3-bromo-2-methylbenzoic acid (4.9g, 22.4mmol), palladium / carbon (1.12mmol), sodium carbonate (4.75g, 44.8mmol) in 500mL reaction flask (reaction system pH value is 8-9 ), sodium tetraphenylborate (2.0 g, 6.05 mmol) and water (125 mL). The reaction mixture was stirred and refluxed for 3 hours. The reaction mixture was poured into 2N hydrochloric acid, the product was extracted with ethyl acetate (3×150 mL), the organic layers were combined, dried and concentrated to give the title compound (92% yield).

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Abstract

The invention discloses a preparation method of 2-methyl-3-biphenylmethanol, which comprises the following steps: carrying out a Suzuki coupling reaction between 3-bromo-2-methylbenzoic acid and phenyl substituted boric acid or phenyl substituted borate to obtain 3-phenyl-2-methylbenzoic acid, and then carrying out a reduction reaction to obtain 2-methyl-3-biphenylmethanol, wherein the Suzuki coupling reaction is carried out at 10-150 DEG C for 1-12 hours under the action of an alkali. 3-phenyl-2-methylbenzoic acid can be directly reduced with a reducing agent such as borane and lithium aluminium hydride to obtain 2-methyl-3-biphenylmethanol.

Description

technical field [0001] The present invention relates to the preparation method of novel 2-methyl-3-phenylbenzyl alcohol. Background technique [0002] Bifenthrin is a highly efficient synthetic pyrethrin insecticide and acaricide. It has contact killing and stomach poisoning effects, and has no systemic and fumigation effects. It has a broad insecticidal spectrum and has good control effect on mites. Acts quickly. It does not move in the soil, is safer for the environment, and has a long residual period. [0003] Bifenthrin was first developed by FMC Crop. It can be used as a high-efficiency insecticide and acaricide. As early as 1978, John F.Engel (FMC Corp.) provided the synthesis of bifenthrin and its Applied research on biological activity. [0004] There are various methods for the synthesis of fenthrin, such as Sagami Chemical Research Center, US4864052 (1989); FMC Corporation, US 4473709 (1984); FMC Corporation, US 4395567 (1983). Wherein the most suitable for ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/24C07C29/147
Inventor 吴浩王良清黄民富罗世英王彦强
Owner NUTRICHEM LAB CO LTD
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