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Telescoping synthesis of 2-methoxymethyl-p-phenylenediamine

A technology of phenylenediamine and aniline, which is applied in the field of preparing 2-substituted-1, and can solve the problems of unsatisfactory synthesis and the like

Inactive Publication Date: 2019-11-01
WELLA OPERATIONS US LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The aforementioned prior synthesis to obtain 2-alkoxymethyl-1,4-phenylenediamines, their derivatives and their salts is not entirely satisfactory

Method used

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  • Telescoping synthesis of 2-methoxymethyl-p-phenylenediamine
  • Telescoping synthesis of 2-methoxymethyl-p-phenylenediamine
  • Telescoping synthesis of 2-methoxymethyl-p-phenylenediamine

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Embodiment

[0083] The following are non-limiting examples of compositions of the invention. These examples are given for the purpose of illustration only and are not to be construed as limiting the invention, since many variations thereof are possible without departing from the spirit and scope of the invention, which will be recognized by ordinary skill in the art recognized by personnel. All concentrations are listed in percent by weight unless specifically stated otherwise.

[0084] 1.1 Placing 2-nitrobenzyl alcohol (VI) to start to prepare 2-methoxymethyl-nitrobenzene (VII)

[0085] 2-Nitrobenzyl alcohol (100 g, 0.653 moles) was partitioned between 50% NaOH (136 g, 1.7 moles) and petroleum ether (500 mL). Via addition funnel (moderate rate), benzyltriethylammonium chloride (2 g) was added followed by dimethyl sulfate (106.4 g, 0.84 mol). The mixture was stirred (mechanically) until complete. Dimethyl sulfate (10 mL) was added and the reaction was stirred for 1 hour. Excess dim...

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Abstract

A telescoping process for the preparation of 2-methoxymethyl-p-phenylenediamine, a cosmetically acceptable salt thereof, or mixture thereof is disclosed. The process according to the present inventionis a particularly cost effective process in that it avoids sophisticated chemical steps which requires special equipment or expensive catalysts and in that it comprises a recycling step of one of thestarting materials, namely 2-methoxymethylaniline.

Description

[0001] The application date is October 29, 2015, the international application number is PCT / US2015 / 058047, the Chinese national application number is 201580059795.6 and the invention name is "for the preparation of 2-substituted-1,4-phenylenediamine and The divisional application of the application of "method of its salt". technical field [0002] The present invention relates to a process for the preparation of 2-substituted-1,4-phenylenediamines or salts thereof. These compounds can be used as coupling agents and / or primary intermediates in compositions for dyeing keratin fibers. Background technique [0003] 2-Substituted-1,4-phenylenediamines, such as 2-methoxymethyl-1,4-phenylenediamine, and their cosmetically acceptable salts, are useful as primary intermediates in oxidative chromotherapy body. [0004] Although the diazotization route to p-phenylenediamine (PPD) is known (EP 0052511 A1) and it has been successfully used for the manufacture of PPD, it is also well k...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/08C07C217/76
CPCC07C213/02C07C213/06C07C245/08C07C245/20C07C245/24C07C217/76C07C215/68
Inventor 加里·史蒂文·加雷特海克·阿贝尔阿明·奥桑约翰·米歇尔·戈德利克布里安·帕特里克·墨菲马库斯·施佩克巴切尔英戈·赖因霍尔德·韦伯
Owner WELLA OPERATIONS US LLC
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