CN115974647A - Method for preparing benvolyl alcohol by using tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol as raw material - Google Patents
Method for preparing benvolyl alcohol by using tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol as raw material Download PDFInfo
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- CN115974647A CN115974647A CN202211547940.3A CN202211547940A CN115974647A CN 115974647 A CN115974647 A CN 115974647A CN 202211547940 A CN202211547940 A CN 202211547940A CN 115974647 A CN115974647 A CN 115974647A
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- phenyl
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- tetrahydro
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- UUQVBQLAIFOJHO-UHFFFAOYSA-N 4-methyl-2-phenyloxan-4-ol Chemical compound C1C(C)(O)CCOC1C1=CC=CC=C1 UUQVBQLAIFOJHO-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 17
- 239000002994 raw material Substances 0.000 title claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 31
- 239000003054 catalyst Substances 0.000 claims abstract description 27
- XBICAVJSPSLHFO-UHFFFAOYSA-N 2-phenyl-3,4-dihydro-2h-pyran Chemical compound O1C=CCCC1C1=CC=CC=C1 XBICAVJSPSLHFO-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000000543 intermediate Substances 0.000 claims abstract description 18
- 230000002378 acidificating effect Effects 0.000 claims abstract description 15
- 238000010438 heat treatment Methods 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000012074 organic phase Substances 0.000 claims abstract description 7
- 238000010992 reflux Methods 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 238000001914 filtration Methods 0.000 claims abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical group [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 8
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000002808 molecular sieve Substances 0.000 claims description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 5
- 239000011973 solid acid Substances 0.000 claims description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- 229920001429 chelating resin Polymers 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 239000005995 Aluminium silicate Substances 0.000 claims description 3
- QCSSZLVGDKWJMK-UHFFFAOYSA-N CCCCCO.c1ccccc1 Chemical compound CCCCCO.c1ccccc1 QCSSZLVGDKWJMK-UHFFFAOYSA-N 0.000 claims description 3
- 239000007868 Raney catalyst Substances 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 235000012211 aluminium silicate Nutrition 0.000 claims description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 3
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052681 coesite Inorganic materials 0.000 claims description 2
- 229910052593 corundum Inorganic materials 0.000 claims description 2
- 229910052906 cristobalite Inorganic materials 0.000 claims description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052682 stishovite Inorganic materials 0.000 claims description 2
- 229910052905 tridymite Inorganic materials 0.000 claims description 2
- 229910001845 yogo sapphire Inorganic materials 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 abstract description 6
- 239000000047 product Substances 0.000 abstract description 5
- 239000007788 liquid Substances 0.000 abstract description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 239000003205 fragrance Substances 0.000 description 5
- 241000220317 Rosa Species 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OXYRENDGHPGWKV-UHFFFAOYSA-N 3-methyl-5-phenylpentan-1-ol Chemical compound OCCC(C)CCC1=CC=CC=C1 OXYRENDGHPGWKV-UHFFFAOYSA-N 0.000 description 1
- DPZMVZIQRMVBBW-UHFFFAOYSA-N 5-Phenyl-1-pentanol Chemical compound OCCCCCC1=CC=CC=C1 DPZMVZIQRMVBBW-UHFFFAOYSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- -1 benzyl amyl Chemical group 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- QVDTXNVYSHVCGW-ONEGZZNKSA-N isopentenol Chemical compound CC(C)\C=C\O QVDTXNVYSHVCGW-ONEGZZNKSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
The invention discloses a method for preparing benfopentanol by taking tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol as a raw material, which comprises the following steps: adding a solvent and an acidic catalyst into a reaction kettle, heating to reflux, dropwise adding tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol, continuously separating water in the system, reacting until the GC content of the raw material is less than 0.5%, filtering the acidic catalyst, and directly rectifying to obtain a phenyldihydropyran intermediate; directly putting the phenyl dihydropyran intermediates and the hydrogenation catalyst into a hydrogenation kettle, heating to carry out hydrogenation reaction, filtering the obtained hydrogenation catalyst to be applied mechanically after the phenyl dihydropyran intermediates are less than 0.5 percent, and directly rectifying an organic phase to obtain the finished product of the benopentanol. The invention recycles the by-products of the original reaction, thereby greatly reducing the liquid volume of the reaction kettle and the economic loss.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, relates to preparation of benfopentanol, and particularly relates to a method for preparing benfopentanol by taking tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol as a raw material.
Background
3-methyl-5-phenyl-pentanol, commonly known as benzole pentanol, is a common series of rose fragrance perfumes. The benenolyl alcohol is a raw material with a transparent and fresh rose fragrance, and is a common rose fragrance series perfume. Meanwhile, fresh and rich effects can be brought to the flowery flavor and the citrus formula. The fragrance of the benfotanol has different persistence and has the fragrance of the rose essential oil, so the benfotanol is widely applied to daily chemical products and personal care. Therefore, the industrial production of the benopentanol has important application value.
The prior method for synthesizing the benfoamyl alcohol mainly comprises the steps of firstly carrying out condensation reaction on benzaldehyde and 3-methyl-3-butylene-1-alcohol to generate a corresponding phenyl dihydropyran intermediate, and then carrying out ring opening to obtain a product of the benfoamyl alcohol. Chinese patent (CN 102731260A) also produces phenyldihydropyran by the reacidification of benzaldehyde and isopentenol under acidic condition, and then produces the benzyl amyl alcohol by hydrogenation under nickel catalyst. Chinese patent (CN 104876800A) takes phenyldihydropyran as a substrate, adopts a secondary hydrogenation technology, and uses Raney nickel and palladium carbon catalysts in sequence to ensure higher hydrogenation yield.
In the above method, due to the reversibility of the first condensation reaction, the condensation of benzaldehyde and 3-methyl-3-buten-1-ol is often accompanied by the production of 3-6% of by-product tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol, which cannot be directly ring-opened to the cloneopentanol under the action of hydrogen and catalyst. The generation of the by-product tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol influences the reaction yield, increases the reaction kettle liquid rate and brings more economic loss.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a method for preparing the benzolpentanol by taking tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol as a raw material. The invention recycles the by-products of the original reaction, thereby greatly reducing the liquid volume of the reaction kettle and the economic loss.
The invention is realized by the following technical scheme:
the method for preparing the benfopentanol by taking the tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol as the raw material comprises the following steps:
(1) Adding a solvent and an acidic catalyst into a reaction kettle, heating to reflux, dropwise adding tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol, continuously separating water in the system, reacting until the GC content of the raw material is less than 0.5%, filtering the acidic catalyst, and directly rectifying to obtain a phenyldihydropyran intermediate;
(2) Directly putting the phenyl dihydropyran intermediates and the hydrogenation catalyst into a hydrogenation kettle, heating to carry out hydrogenation reaction, filtering the obtained hydrogenation catalyst to be applied mechanically after the phenyl dihydropyran intermediates are less than 0.5 percent, and directly rectifying an organic phase to obtain the finished product of the benopentanol.
The reaction equation is as follows:
the invention further improves the scheme as follows:
the acidic catalyst is a solid acid or an acidic resin.
Further, the solid acid is one or a mixture of more than two of montmorillonite, kaolin, siO2-Al2O3, zrO2-SiO2, ZSM-5 molecular sieve or Y-type molecular sieve.
Further, the acidic resin is one or a mixture of more than two of Amberlyst 15, amberlyst 25 or NKC-9.
Further, the solvent is one or a mixture of more than two of toluene, xylene, trimethylbenzene, petroleum ether, cyclohexane, n-hexane and n-octane.
Further, the hydrogenation catalyst is Raney nickel.
Further, the mass of the acid catalyst is 0.01-1% of that of tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol; the mass of the solvent is 0.05-10 times of that of tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol. (ii) a The mass of the hydrogenation catalyst is 0.001-1% of that of the phenyldihydropyrane intermediate.
Furthermore, the hydrogenation reaction temperature is 50-150 ℃, and the hydrogenation reaction pressure is 0.5-5Mpa.
Compared with the prior art, the invention has the following beneficial effects:
(1) The raw material used in the invention is the byproduct hydrogen-4-methyl-2-phenyl-2H-pyran-4-ol in the process of synthesizing the benfoamyl alcohol, the byproduct is recycled, the atomic economy concept is met, and the economic loss is reduced.
(2) The acid catalyst used in the invention is solid acid or acid resin catalyst, the hydrogenation catalyst is cheap Raney nickel catalyst, and the two catalysts can be directly filtered and reused after reaction for more than 15 times, thus greatly reducing the production cost. And water washing is not needed after the reaction, so that the generation of generated wastewater is reduced.
(3) The invention has high conversion rate and good selectivity, the selectivity of both the two steps of reactions exceeds 99 percent, and the comprehensive yield is 96 percent.
Detailed Description
The present invention will be described in detail with reference to specific examples.
Example 1
(1) 220g of toluene and 15g of acidic resin Amberlyst are added into a 2L jacketed kettle, heating reflux is carried out, 450g of tetrahydro-4-methyl-2-phenyl-2H-pyran-4-alcohol is dripped into the reaction kettle within 3H, and water generated in the reaction process is continuously separated out. After the dropwise addition is finished, the temperature is kept for 3h, after the GC content of the raw material is less than 0.5 percent, the catalyst is directly filtered and recovered, the toluene is recovered by organic phase vacuum distillation, the phenyl dihydropyran intermediate 406.8g is obtained by distillation, and the GC content is 99 percent. (2) And putting 406.8g of the obtained phenyldihydropyran intermediate into a 1L hydrogenation kettle, adding 4.1g of Raney nickel catalyst, heating to 100 ℃, starting hydrogenation under the pressure of 0.8-1MPa, reacting for 7 hours, and stopping reaction when about 0.5 percent of GC content of phenyldihydropyran remains. After the reaction is finished, the reaction materials are filtered and directly rectified to obtain 380g of finished product of the benfoamyl alcohol, the GC content is 99 percent, and the two-step comprehensive yield is 91 percent.
Example 2
(1) 150g of dimethylbenzene and 15g of ZSM-5 molecular sieve are added into a 2L jacket kettle, heating and refluxing are carried out, 450g of tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol is dripped into a reaction kettle within 6H, and water generated in the reaction process is continuously separated out. After the dropwise addition is finished, the temperature is kept for 4 hours, after the GC content of the raw material is less than 0.5 percent, the catalyst is directly filtered and recovered, xylene is recovered by organic phase vacuum distillation, 400.5g of phenyldihydropyran intermediate is obtained by rectification, and the GC content is 99 percent. (2) Putting 400.5g of the obtained phenyldihydropyran intermediate into a 1L hydrogenation kettle, adding 8.5g of Raney nickel catalyst, heating to 100 ℃, starting hydrogenation under the pressure of 0.8-1MPa, reacting for 5h, and stopping reaction when about 0.5% of GC content of phenyldihydropyran remains. After the reaction is finished, the reaction mass is filtered and then rectified to obtain 396g of the benayl pentanol, the GC content is 99 percent, and the comprehensive yield of the two steps is 94.9 percent.
Example 3
(1) 350g of petroleum ether and 30g of kaolin are added into a 2L jacketed kettle, heating reflux is carried out, 450g of tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol is dripped into a reaction kettle within 3 hours, and water generated in the reaction process is continuously separated out. After the dropwise addition is finished, the temperature is kept for 5h, after the GC content of the raw material is less than 0.5%, the catalyst is directly filtered and recovered, the organic phase is subjected to vacuum distillation to recover petroleum ether, the rectification is carried out to obtain 400.1g of a phenyldihydropyran intermediate, and the GC content is 99%. (2) Putting 400.1g of the obtained phenyldihydropyrane into a 1L hydrogenation kettle, adding 13g of Raney nickel catalyst, heating to 120 ℃, reacting for 3 hours when the pressure is 0.8-1.5MPa, and stopping the reaction when about 0.5% of the GC content of the phenyldihydropyrane remains. After the reaction is finished, the reaction mass is filtered and then rectified to obtain 344g of the benzole pentanol with 99 percent of GC content and 82.6 percent of two-step comprehensive yield.
Example 4
(1) 450g of cyclohexane and 25 10g of acidic resin Amberlyst are added into a 2L jacketed kettle, heating reflux is carried out, 450g of tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol is added into the reaction kettle in a dropwise manner within 6H, and water produced in the reaction process is continuously separated out. After the dropwise addition is finished, the temperature is kept for 2h, after the GC content of the raw material is less than 0.5%, the catalyst is directly filtered and recovered, cyclohexane is recovered by organic phase vacuum distillation, 407.4g of phenyldihydropyrane intermediate is obtained by rectification, and the GC content is 99%. (2) Putting 407.4g of the obtained phenyldihydropyrane into a 1L hydrogenation kettle, adding 13g of Raney nickel catalyst, heating to 120 ℃, starting hydrogenation under the pressure of 0.8-1.5MPa, reacting for 3h, and stopping reaction when the GC content of the phenyldihydropyrane is about 0.5 percent. After the reaction is finished, the reaction mass is filtered and then rectified to obtain the benfoamyl alcohol 399.6g with the GC content of 99 percent and the two-step comprehensive yield of 96 percent.
The above embodiments are merely illustrative of the technical concepts and features of the present invention, and the purpose of the embodiments is to enable those skilled in the art to understand the contents of the present invention and implement the present invention, and not to limit the protection scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered in the protection scope of the present invention.
Claims (8)
1. The method for preparing the benfopentanol by taking the tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol as the raw material is characterized by comprising the following steps of:
(1) Adding a solvent and an acidic catalyst into a reaction kettle, heating to reflux, dropwise adding tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol, continuously separating water in the system, reacting until the GC content of the raw material is less than 0.5%, filtering the acidic catalyst, and directly rectifying to obtain a phenyldihydropyran intermediate;
(2) Directly putting the phenyl dihydropyran intermediates and the hydrogenation catalyst into a sleeve hydrogenation kettle, heating to carry out hydrogenation reaction, filtering the obtained hydrogenation catalyst for application after the content of the phenyl dihydropyran intermediates is less than 0.5%, and directly rectifying an organic phase to obtain the finished product of the benzole pentanol.
2. The process of claim 1 for the preparation of benfopentanol starting from tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol, characterized in that: the acidic catalyst is a solid acid or an acidic resin.
3. The process of claim 2 for the preparation of benfopentanol starting from tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol, characterized in that: the solid acid is one or more of montmorillonite, kaolin, siO2-Al2O3, zrO2-SiO2, ZSM-5 molecular sieve or Y-type molecular sieve.
4. The process of claim 2 for the preparation of benfopentanol starting from tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol, characterized in that: the acidic resin is one or more of Amberlyst 15, amberlyst 25 or NKC-9.
5. The process of claim 1 for the preparation of benfopentanol starting from tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol, characterized in that: the solvent is one or a mixture of more than two of toluene, dimethylbenzene, trimethylbenzene, petroleum ether, cyclohexane, n-hexane and n-octane.
6. The process of claim 1 for the preparation of benzolopentanol starting from tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol, characterized in that: the hydrogenation catalyst is Raney nickel.
7. The process of claim 1 for the preparation of benfopentanol starting from tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol, characterized in that: the mass of the acid catalyst is 0.01-1% of that of tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol; the mass of the solvent is 0.05 to 10 times of that of tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol, and the mass of the hydrogenation catalyst is 0.001 to 1 percent of that of the phenyldihydropyran intermediate.
8. The process of claim 1 for the preparation of benzolopentanol starting from tetrahydro-4-methyl-2-phenyl-2H-pyran-4-ol, characterized in that: the hydrogenation reaction temperature is 50-150 ℃, and the hydrogenation reaction pressure is 0.5-5Mpa.
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