CN105399608A - Synthetic method for 2,5-dichloro-4-(4-chlorophenoxyl)-acetophenone - Google Patents
Synthetic method for 2,5-dichloro-4-(4-chlorophenoxyl)-acetophenone Download PDFInfo
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- CN105399608A CN105399608A CN201510920132.0A CN201510920132A CN105399608A CN 105399608 A CN105399608 A CN 105399608A CN 201510920132 A CN201510920132 A CN 201510920132A CN 105399608 A CN105399608 A CN 105399608A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/64—Preparation of O-metal compounds with O-metal group bound to a carbon atom belonging to a six-membered aromatic ring
- C07C37/66—Preparation of O-metal compounds with O-metal group bound to a carbon atom belonging to a six-membered aromatic ring by conversion of hydroxy groups to O-metal groups
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- C07—ORGANIC CHEMISTRY
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- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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Abstract
The invention discloses a synthetic method for 2,5-dichloro-4-(4-chlorophenoxyl)-acetophenone, which belongs to the field of chemical synthesis. The synthetic method comprises the following steps: adding sodium hydroxide into p-chlorophenol so as to obtain sodium p-chlorophenolate; then adding 1,3,5-trichlorobenzene, 1-methyl-2-pyrrolidone and a catalyst cuprous oxide so as to obtain a faint yellow viscous liquid; adding dichloroethane, an aluminum chloride catalyst and acetic anhydride into a bottle and slowing adding hydrochloric acid into the bottle in ice water with a temperature of 0 DEG C; and successively carrying out crystal precipitation, pumping filtration, cleaning, drying and recrystallization so as to obtain a 2,5-dichloro-4-(4-chlorophenoxyl)-acetophenone solid.
Description
Technical field
The invention discloses a kind of synthetic method of 2,5-bis-chloro-4-(4-chlorophenoxy)-methyl phenyl ketone, belong to the field of chemical synthesis.
Background technology
Difenoconazole is a kind of ultra-high efficiency, wide spectrum, interior absorption three series bactericidal agent, the restraining effect strong to the sporulation of phytopathogen, and in controlling disease process, three large effects showing prevention, treat, root out.
The synthetic method of classical diaryl ether is Ullmann reaction, and reactive behavior is subject to the impact of several factors, as the kind of halogen in halogenated aryl hydrocarbon, and the use etc. of the selection of solvent, catalyzer, part.Generally the reactive behavior of iodo and aryl bromide is much larger than chlorinated aromatic hydrocarbons.Can the selection of solvent has influence on reacting phase uniform and stable, and can reactant fully contact and make to react completely, and how temperature of reaction controls, and whether there is solvent effect.Unmalm reaction is the method for the most directly synthesis of diaryl ethers, and be up to the present still widely used in organic synthesis, but the shortcoming of this reaction is also obvious: the use of the phenol sodium that a. is greatly excessive makes reaction needed carry out under stricter anhydrous and oxygen-free condition, and can not be used for the synthesis of diaryl ether when substrate having the group to alkaline condition sensitivity; B. reaction needed is carried out at a higher temperature, limits the range of application of reaction; C. need in reaction to use a large amount of intensive polar solvents as DMF, DMSO or HMPA etc., make the last handling process of reaction quite numerous and diverse: the use of the stoichiometric mantoquita of d does not meet the requirement of existing building-up reactions to reaction environment friendly; E. must with activating group on halogenated aryl hydrocarbon, nonetheless, the yield value of reaction is also only medium, and poor repeatability.The existence of these shortcomings greatly limit the application of Ullmann reaction in organic synthesis.
Summary of the invention
The invention provides the synthetic method of 2,5-bis-chloro-4-(4-the chlorophenoxy)-methyl phenyl ketone that a kind of reaction conditions is gentle, yield is high.
For achieving the above object, the synthetic route of the chloro-4-of the present invention 2,5-bis-(4-chlorophenoxy)-methyl phenyl ketone is:
The building-up process of 2,5-bis-chloro-4-(4-the chlorophenoxy)-methyl phenyl ketone that the present invention relates to comprises the following steps:
(1) in the 250mL there-necked flask that prolong, thermometer, agitator are housed, add the benzene of 50 ~ 60mL, the sodium hydroxide solution of 10 ~ 15mL massfraction 40% and the para-chlorophenol of 10 ~ 12g wherein, water trap is installed, there-necked flask is put into water-bath, at 85 ~ 90 DEG C of temperature, carry out backflow 40 ~ 50min while stirring, after backflow terminates, remove water trap;
(2) 10 ~ 12g1 is added by above-mentioned there-necked flask, 3, 5-trichlorobenzene, add 10 ~ 15mL1-methyl-2-again and adjoin pyrrolidone and catalyst oxidation is cuprous, continue to be warming up to 100 ~ 105 DEG C, backflow 4 ~ 5h is carried out under the condition stirred, room temperature is cooled to after backflow, reaction solution Büchner funnel in bottle is carried out suction filtration, be 5 ~ 6 by the salt acid for adjusting pH value obtaining filtrate and drip wherein massfraction 15 ~ 20%, afterwards the filtrate after adjustment is moved in separating funnel, removing aqueous phase, by the oil phase underpressure distillation obtained, collect cut, obtain light yellow viscous liquid,
(3) get in the there-necked flask of 30 ~ 35mL product obtained above and 250mL, ethylene dichloride and 5 ~ 6g aluminum chloride catalyst is added again in bottle, the diacetyl oxide of 18 ~ 20mL is added in dropping funnel, diacetyl oxide drips off by the condition stirred in 30 ~ 40min, stirring reaction 1 ~ 2h is carried out after dropping, the mixed solution obtained after reaction is poured in the beaker of 250mL, beaker is put into the frozen water of 0 DEG C, and the lower hydrochloric acid slowly adding 20 ~ 25mL massfraction 15% stirred;
(4) mixed solution after above-mentioned dripping off is proceeded in separating funnel, pH to 7 is regulated with massfraction 40% potassium hydroxide solution, removing aqueous phase, remaining organic layer distilled water is washed 2 ~ 4 times repeatedly, afterwards organic phase is placed in rotating pressure-decreasing evaporimeter, 60 DEG C are progressively warming up to from 25 DEG C, temperature rise rate is 3 DEG C/min, flask is put into the refrigerator and cooled of-5 DEG C but, separate out white crystal, suction filtration, by solid with after distilled water cleaning 1 ~ 3 time, carry out vacuum-drying, recrystallization is being carried out with tetracol phenixin after drying, vacuum-drying again, 2, the chloro-4-of 5-bis-(4-chlorophenoxy)-methyl phenyl ketone pressed powder.
Specific embodiments
In the 250mL there-necked flask that prolong, thermometer, agitator are housed, add the benzene of 50 ~ 60mL, the sodium hydroxide solution of 10 ~ 15mL massfraction 40% and the para-chlorophenol of 10 ~ 12g wherein, water trap is installed, there-necked flask is put into water-bath, at 85 ~ 90 DEG C of temperature, carry out backflow 40 ~ 50min while stirring, after backflow terminates, remove water trap, by there-necked flask in add 10 ~ 12g1,3,5-trichlorobenzene, add 10 ~ 15mL1-methyl-2-again and adjoin pyrrolidone and catalyst oxidation is cuprous, continue to be warming up to 100 ~ 105 DEG C, backflow 4 ~ 5h is carried out under the condition stirred, room temperature is cooled to after backflow, reaction solution Büchner funnel in bottle is carried out suction filtration, is 5 ~ 6 by the salt acid for adjusting pH value obtaining filtrate and drip wherein massfraction 15 ~ 20%, moves in separating funnel afterwards by the filtrate after regulating, removing aqueous phase, by the oil phase underpressure distillation obtained, collect cut, obtain light yellow viscous liquid, get in the there-necked flask of product that 30 ~ 35mL obtains and 250mL, ethylene dichloride and 5 ~ 6g aluminum chloride catalyst is added again in bottle, the diacetyl oxide of 18 ~ 20mL is added in dropping funnel, diacetyl oxide drips off by the condition stirred in 30 ~ 40min, stirring reaction 1 ~ 2h is carried out after dropping, the mixed solution obtained after reaction is poured in the beaker of 250mL, beaker is put into the frozen water of 0 DEG C, and the lower hydrochloric acid slowly adding 20 ~ 25mL massfraction 15% stirred, mixed solution after dripping off is proceeded in separating funnel, pH to 7 is regulated with massfraction 40% potassium hydroxide solution, removing aqueous phase, remaining organic layer distilled water is washed 2 ~ 4 times repeatedly, afterwards organic phase is placed in rotating pressure-decreasing evaporimeter, 60 DEG C are progressively warming up to from 25 DEG C, temperature rise rate is 3 DEG C/min, flask is put into the refrigerator and cooled of-5 DEG C but, separate out white crystal, suction filtration, by solid with after distilled water cleaning 1 ~ 3 time, carry out vacuum-drying, recrystallization is being carried out with tetracol phenixin after drying, vacuum-drying again, 2, the chloro-4-of 5-bis-(4-chlorophenoxy)-methyl phenyl ketone pressed powder.
Example 1
In the 250mL there-necked flask that prolong, thermometer, agitator are housed, add the benzene of 50mL, the sodium hydroxide solution of 10mL massfraction 40% and the para-chlorophenol of 10g wherein, water trap is installed, there-necked flask is put into water-bath, at 85 DEG C of temperature, carry out backflow 40min while stirring, after backflow terminates, remove water trap, by there-necked flask in add 10g1,3,5-trichlorobenzene, add 10mL1-methyl-2-again and adjoin pyrrolidone and catalyst oxidation is cuprous, continue to be warming up to 100 DEG C, backflow 4h is carried out under the condition stirred, room temperature is cooled to after backflow, reaction solution Büchner funnel in bottle is carried out suction filtration, is 5 by the salt acid for adjusting pH value obtaining filtrate and drip wherein massfraction 15%, moves in separating funnel afterwards by the filtrate after regulating, removing aqueous phase, by the oil phase underpressure distillation obtained, collect cut, obtain light yellow viscous liquid, get in the there-necked flask of product that 30mL obtains and 250mL, ethylene dichloride and 5g aluminum chloride catalyst is added again in bottle, the diacetyl oxide of 18mL is added in dropping funnel, diacetyl oxide drips off by the condition stirred in 30min, stirring reaction 1h is carried out after dropping, the mixed solution obtained after reaction is poured in the beaker of 250mL, beaker is put into the frozen water of 0 DEG C, and the lower hydrochloric acid slowly adding 20mL massfraction 15% stirred, mixed solution after dripping off is proceeded in separating funnel, pH to 7 is regulated with massfraction 40% potassium hydroxide solution, removing aqueous phase, remaining organic layer distilled water is washed 2 times repeatedly, afterwards organic phase is placed in rotating pressure-decreasing evaporimeter, 60 DEG C are progressively warming up to from 25 DEG C, temperature rise rate is 3 DEG C/min, flask is put into the refrigerator and cooled of-5 DEG C but, separate out white crystal, suction filtration, after solid distilled water is cleaned 1 time, carry out vacuum-drying, recrystallization is being carried out with tetracol phenixin after drying, vacuum-drying again, 2, the chloro-4-of 5-bis-(4-chlorophenoxy)-methyl phenyl ketone pressed powder.
Example 2
In the 250mL there-necked flask that prolong, thermometer, agitator are housed, add the benzene of 55mL, the sodium hydroxide solution of 13mL massfraction 40% and the para-chlorophenol of 11g wherein, water trap is installed, there-necked flask is put into water-bath, at 87 DEG C of temperature, carry out backflow 45min while stirring, after backflow terminates, remove water trap, by there-necked flask in add 11g1,3,5-trichlorobenzene, add 13mL1-methyl-2-again and adjoin pyrrolidone and catalyst oxidation is cuprous, continue to be warming up to 103 DEG C, backflow 4.5h is carried out under the condition stirred, room temperature is cooled to after backflow, reaction solution Büchner funnel in bottle is carried out suction filtration, is 5.5 by the salt acid for adjusting pH value obtaining filtrate and drip wherein massfraction 17%, moves in separating funnel afterwards by the filtrate after regulating, removing aqueous phase, by the oil phase underpressure distillation obtained, collect cut, obtain light yellow viscous liquid, get in the there-necked flask of product that 33mL obtains and 250mL, ethylene dichloride and 5.5g aluminum chloride catalyst is added again in bottle, the diacetyl oxide of 19mL is added in dropping funnel, diacetyl oxide drips off by the condition stirred in 35min, stirring reaction 1.5h is carried out after dropping, the mixed solution obtained after reaction is poured in the beaker of 250mL, beaker is put into the frozen water of 0 DEG C, and the lower hydrochloric acid slowly adding 23mL massfraction 15% stirred, mixed solution after dripping off is proceeded in separating funnel, pH to 7 is regulated with massfraction 40% potassium hydroxide solution, removing aqueous phase, remaining organic layer distilled water is washed 3 times repeatedly, afterwards organic phase is placed in rotating pressure-decreasing evaporimeter, 60 DEG C are progressively warming up to from 25 DEG C, temperature rise rate is 3 DEG C/min, flask is put into the refrigerator and cooled of-5 DEG C but, separate out white crystal, suction filtration, after solid distilled water is cleaned 2 times, carry out vacuum-drying, recrystallization is being carried out with tetracol phenixin after drying, vacuum-drying again, 2, the chloro-4-of 5-bis-(4-chlorophenoxy)-methyl phenyl ketone pressed powder.
Example 3
In the 250mL there-necked flask that prolong, thermometer, agitator are housed, add the benzene of 60mL, the sodium hydroxide solution of 15mL massfraction 40% and the para-chlorophenol of 12g wherein, water trap is installed, there-necked flask is put into water-bath, at 90 DEG C of temperature, carry out backflow 50min while stirring, after backflow terminates, remove water trap, by there-necked flask in add 12g1,3,5-trichlorobenzene, add 15mL1-methyl-2-again and adjoin pyrrolidone and catalyst oxidation is cuprous, continue to be warming up to 105 DEG C, backflow 5h is carried out under the condition stirred, room temperature is cooled to after backflow, reaction solution Büchner funnel in bottle is carried out suction filtration, is 6 by the salt acid for adjusting pH value obtaining filtrate and drip wherein massfraction 20%, moves in separating funnel afterwards by the filtrate after regulating, removing aqueous phase, by the oil phase underpressure distillation obtained, collect cut, obtain light yellow viscous liquid, get in the there-necked flask of product that 35mL obtains and 250mL, ethylene dichloride and 6g aluminum chloride catalyst is added again in bottle, the diacetyl oxide of 20mL is added in dropping funnel, diacetyl oxide drips off by the condition stirred in 40min, stirring reaction 2h is carried out after dropping, the mixed solution obtained after reaction is poured in the beaker of 250mL, beaker is put into the frozen water of 0 DEG C, and the lower hydrochloric acid slowly adding 25mL massfraction 15% stirred, mixed solution after dripping off is proceeded in separating funnel, pH to 7 is regulated with massfraction 40% potassium hydroxide solution, removing aqueous phase, remaining organic layer distilled water is washed 4 times repeatedly, afterwards organic phase is placed in rotating pressure-decreasing evaporimeter, 60 DEG C are progressively warming up to from 25 DEG C, temperature rise rate is 3 DEG C/min, flask is put into the refrigerator and cooled of-5 DEG C but, separate out white crystal, suction filtration, after solid distilled water is cleaned 3 times, carry out vacuum-drying, recrystallization is being carried out with tetracol phenixin after drying, vacuum-drying again, 2, the chloro-4-of 5-bis-(4-chlorophenoxy)-methyl phenyl ketone pressed powder.
Claims (1)
1. the synthetic method of bis-chloro-4-(4-chlorophenoxy)-methyl phenyl ketone, is characterized in that the synthesis of the chloro-4-of 2,5-bis-(4-chlorophenoxy)-methyl phenyl ketone:
(1) in the 250mL there-necked flask that prolong, thermometer, agitator are housed, add the benzene of 50 ~ 60mL, the sodium hydroxide solution of 10 ~ 15mL massfraction 40% and the para-chlorophenol of 10 ~ 12g wherein, water trap is installed, there-necked flask is put into water-bath, at 85 ~ 90 DEG C of temperature, carry out backflow 40 ~ 50min while stirring, after backflow terminates, remove water trap;
(2) 10 ~ 12g1 is added by above-mentioned there-necked flask, 3, 5-trichlorobenzene, add 10 ~ 15mL1-methyl-2-again and adjoin pyrrolidone and catalyst oxidation is cuprous, continue to be warming up to 100 ~ 105 DEG C, backflow 4 ~ 5h is carried out under the condition stirred, room temperature is cooled to after backflow, reaction solution Büchner funnel in bottle is carried out suction filtration, be 5 ~ 6 by the salt acid for adjusting pH value obtaining filtrate and drip wherein massfraction 15 ~ 20%, afterwards the filtrate after adjustment is moved in separating funnel, removing aqueous phase, by the oil phase underpressure distillation obtained, collect cut, obtain light yellow viscous liquid,
(3) get in the there-necked flask of 30 ~ 35mL product obtained above and 250mL, ethylene dichloride and 5 ~ 6g aluminum chloride catalyst is added again in bottle, the diacetyl oxide of 18 ~ 20mL is added in dropping funnel, diacetyl oxide drips off by the condition stirred in 30 ~ 40min, stirring reaction 1 ~ 2h is carried out after dropping, the mixed solution obtained after reaction is poured in the beaker of 250mL, beaker is put into the frozen water of 0 DEG C, and the lower hydrochloric acid slowly adding 20 ~ 25mL massfraction 15% stirred;
(4) mixed solution after above-mentioned dripping off is proceeded in separating funnel, pH to 7 is regulated with massfraction 40% potassium hydroxide solution, removing aqueous phase, remaining organic layer distilled water is washed 2 ~ 4 times repeatedly, afterwards organic phase is placed in rotating pressure-decreasing evaporimeter, 60 DEG C are progressively warming up to from 25 DEG C, temperature rise rate is 3 DEG C/min, flask is put into the refrigerator and cooled of-5 DEG C but, separate out white crystal, suction filtration, by solid with after distilled water cleaning 1 ~ 3 time, carry out vacuum-drying, recrystallization is being carried out with tetracol phenixin after drying, vacuum-drying again, 2, the chloro-4-of 5-bis-(4-chlorophenoxy)-methyl phenyl ketone pressed powder.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1863756A (en) * | 2003-08-07 | 2006-11-15 | 住友化学株式会社 | Process for producing 4-hydroxydiphenyl ether |
| CN104086343A (en) * | 2014-07-07 | 2014-10-08 | 中国科学院山西煤炭化学研究所 | Catalytic synthetic method for diphenyl ether compound |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1863756A (en) * | 2003-08-07 | 2006-11-15 | 住友化学株式会社 | Process for producing 4-hydroxydiphenyl ether |
| CN104086343A (en) * | 2014-07-07 | 2014-10-08 | 中国科学院山西煤炭化学研究所 | Catalytic synthetic method for diphenyl ether compound |
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Application publication date: 20160316 |