CN112321401A - Method for preparing 2-hydroxyethyl phenyl ketone by catalytic oxidation of isochroman - Google Patents

Method for preparing 2-hydroxyethyl phenyl ketone by catalytic oxidation of isochroman Download PDF

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CN112321401A
CN112321401A CN202011250051.1A CN202011250051A CN112321401A CN 112321401 A CN112321401 A CN 112321401A CN 202011250051 A CN202011250051 A CN 202011250051A CN 112321401 A CN112321401 A CN 112321401A
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isochroman
phenyl ketone
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CN112321401B (en
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吴亚
李婧瑶
方荣苗
陈刚
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Xian Shiyou University
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    • C—CHEMISTRY; METALLURGY
    • 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
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
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    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract

A method for preparing 2-hydroxyethyl phenyl ketone by catalytic oxidation of isochroman comprises mixing 1-substituted isochroman with

Description

Method for preparing 2-hydroxyethyl phenyl ketone by catalytic oxidation of isochroman
Technical Field
The invention relates to a method for preparing 2-hydroxyethyl phenyl ketone by catalytic oxidation of isochroman.
Background
2-hydroxyethyl phenyl ketone is an important drug synthesis intermediate, and 2-hydroxyethyl phenyl ketone and its derivatives are commonly used in medicinal chemistry for the synthesis of benzodiazepines and benzodiazepines, analogs of neuroprotectant GYKI52466 and related LY300164 and tofisopam (Acta pharm. sin. B2015, 5, 500; Eur. J. Med. chem.2016,111,103), which have great potential in the treatment of epilepsy, spasticity, chronic pain, neurodegenerative diseases, and the like.
Early reports of the preparation of 2-hydroxyethyl phenyl ketone include osmium tetroxide combined with periodate oxidative cracking of olefin compounds (j.am. chem. soc.2008,130,7198) or nucleophilic addition of isochromanone by grignard reagents followed by hydrolysis (Tetrahedron 2010,66, 3147). However, the method uses raw materials which are complex to prepare, difficult to obtain, and needs expensive catalyst or extremely toxic oxidant osmium tetroxide, which is extremely harmful to the environment.
In 2016, 2-hydroxyethyl phenyl ketone (shown as a formula 1-1) is prepared by taking 1-aryl substituted isochroman as a raw material through laccase catalyzed oxidation reaction by R.Bernini (New J.chem.2016,40,3314). However, the laccase used in the method is easy to inactivate, and simultaneously, a complex auxiliary agent is introduced, so that the reaction time is long, the reaction yield is greatly influenced by the AcO group on the benzene ring, and the method is only suitable for the substrate with the 1-position as the aryl group.
Figure BDA0002771317410000011
Figure BDA0002771317410000021
The topic group of Xiao Jianlianlianlian 2019 uses iron complexes to catalyze oxygen to oxidize 1-substituted isochroman to prepare 2-hydroxyethyl phenyl ketone (shown as formula 1-2) with a yield of 49% -71% (chem. Eur. J.2019,25, 4345-one 4357). In the oxidation process, the catalyst iron complex needs to be added in batches for many times, the reaction time is long, the conversion rate is low, the catalyst system iron complex is sensitive to water, a ligand (shown as a formula L) used for preparing the catalyst is expensive, and the method only provides a substrate with 1-position aryl.
Figure BDA0002771317410000022
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a method for preparing 2-hydroxyethyl phenyl ketone by catalytic oxidation of isochroman, which uses a cheap catalyst, improves the reaction efficiency through simple operation steps, avoids the use of expensive and toxic catalysts or auxiliary agents, and reduces the pollution to the environment.
The invention is realized by the following technical scheme:
a method for preparing 2-hydroxyethyl phenyl ketone by catalytic oxidation of isochroman comprises reacting 1-substituted isochroman as shown in formula (1) with
Figure BDA0002771317410000032
Dissolving acid in an organic solvent, uniformly mixing, or dissolving 1-substituted isochroman as shown in formula (1) and an aryl carbocation compound in an organic solvent, uniformly mixing, reacting at a preset temperature, and separating to obtain 2-hydroxyethyl phenyl ketone as shown in formula (2);
Figure BDA0002771317410000031
wherein A is Ar or R, Ar is any one of phenyl, naphthyl, p-tolyl, o-tolyl, m-tolyl, p-tert-butylphenyl, p-chlorophenyl, p-bromophenyl, p-fluorophenyl, p-nitrophenyl, p-methoxyphenyl, p-trifluoromethylphenyl, m-chlorophenyl and m-nitrophenyl, and R is any one of C1-C6 alkyl, cycloalkyl, styryl, p-toluenyl, p-chlorostyryl and p-nitrobenzylyl; b and C are H or OCH respectively3。
The invention further improves the following steps: said
Figure BDA0002771317410000033
The acid isAny one of C1-C8 alkylsulfonic acid, perfluoroalkyl sulfonic acid, aryl sulfonic acid, camphorsulfonic acid, squaric acid, trifluoroacetic acid and picric acid.
The invention further improves the following steps: the aryl carbonium ion compound is any one of triphenylmethyl tetrafluoroborate, triphenylhexachloroantimonate and triphenylmethyl perchlorate.
The invention further improves the following steps: said 1-substituted isochroman and
Figure BDA0002771317410000034
the molar ratio of the acid or aryl carbenium ion compound is 1 (1-2).
The invention further improves the following steps: the organic solvent is any one of dichloroethane, methane chloride, chloroform, dichloromethane, carbon tetrachloride, acetonitrile, dioxane, tetrahydrofuran, ethyl acetate, cyclohexane, benzene, toluene and xylene.
The invention further improves the following steps: the reaction temperature is 25-80 ℃, and the reaction time is 0.1-12 hours.
Compared with the prior art, the invention has the following beneficial technical effects:
the preparation method of the 2-hydroxyethyl phenyl ketone comprises the steps of carrying out dehydrogenation oxidation on 1-position hydrogen of 1-substituted isochroman under the catalysis of acid or aryl carbenium ion compounds to form carbenium ion intermediates, combining the carbenium ion intermediates with water to form hemiketals, and further carrying out ring opening to form the product 2-hydroxyethyl phenyl ketone. The preparation method provided by the invention does not need to use an oxidant, does not need to use an expensive or toxic catalyst or auxiliary agent, reduces the pollution to the environment, reduces the cost, and has simple operation and high atom economy. The compound synthesized by the invention can be used as a drug synthesis intermediate for synthesizing drugs with potential for treating epilepsy, spasm, chronic pain and neurodegenerative diseases.
Furthermore, the method has the advantages of mild reaction conditions, low reaction temperature, short reaction time and high efficiency.
Detailed Description
The present invention will now be described in further detail with reference to specific examples, which are intended to be illustrative, but not limiting, of the invention.
1-substituted isochroman compounds of the invention and
Figure BDA0002771317410000041
the molar ratio of the acid or the 1-substituted isochroman to the aryl carbenium ion compound is 1 (1-2).
The organic solvent is any one of dichloroethane, methane chloride, chloroform, dichloromethane, carbon tetrachloride, acetonitrile, dioxane, tetrahydrofuran, ethyl acetate, cyclohexane, benzene, toluene and xylene.
Example 1
Taking the preparation of 2-hydroxyethyl benzophenone compound of the following formula as an example, the raw materials and the preparation method thereof are as follows:
Figure BDA0002771317410000051
in example 1, 0.13g (0.6mmol) of 1-phenylisochroman and 0.5mL of 1, 2-dichloroethane were charged into a 50mL reaction tube, the mixture was stirred at room temperature to dissolve the whole raw material, 0.09g (0.6mmol) of trifluoromethanesulfonic acid was further added, the reaction was stopped by stirring at 80 ℃ for 0.5 hour, 2mL of a saturated aqueous solution of sodium hydrogencarbonate was added to the system, extraction was carried out three times with 10mL of ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, suction filtration, concentration, and column chromatography separation (ethyl acetate and n-hexane) of the crude product was carried out to obtain a white solid product, the yield of which was 89%, and the characterization data was:1H NMR(400MHz,CDCl3)δ7.82(dd,J＝8.4,1.3Hz,2H),7.63–7.58(m,1H),7.45(ddd,J＝16.7,8.1,4.1Hz,3H),7.37–7.27(m,3H),3.89(t,J＝6.2Hz,2H),2.95(t,J＝6.2Hz,2H).13C NMR(101MHz,CDCl3)δ198.91,139.04,138.53,137.60,133.46,131.05,131.00,130.62,129.43,128.46,125.64,63.97,36.30.
example 2
Taking the preparation of 2-hydroxyethyl benzophenone compound of the following formula as an example, the raw materials and the preparation method thereof are as follows:
Figure BDA0002771317410000052
in example 2, the trifluoromethanesulfonic acid used in example 1 was replaced with camphorsulfonic acid, the amount was replaced with 2 times the amount of trifluoromethanesulfonic acid, the reaction temperature was replaced with 60 ℃, the reaction time was replaced with 5 hours, and other procedures were the same as in example 1, to prepare a white oily solid product with a yield of 74%, and the obtained product was characterized by a Bruker Avance type superconducting fourier digital nuclear magnetic resonance spectrometer with the following characterization data:1H NMR(400MHz,CDCl3)δ7.82(dd,J＝8.4,1.3Hz,2H),7.63–7.58(m,1H),7.45(ddd,J＝16.7,8.1,4.1Hz,3H),7.37–7.27(m,3H),3.89(t,J＝6.2Hz,2H),2.95(t,J＝6.2Hz,2H).13C NMR(101MHz,CDCl3)δ198.91,139.04,138.53,137.60,133.46,131.05,131.00,130.62,129.43,128.46,125.64,63.97,36.30.
example 3
Taking the preparation of 2-hydroxyethyl benzophenone compound of the following formula as an example, the raw materials and the preparation method thereof are as follows:
Figure BDA0002771317410000061
in example 3, the trifluoromethanesulfonic acid used in example 1 was replaced with an equimolar amount of triphenylmethyltetrafluoroborate, the reaction temperature was replaced with 25 ℃ and the reaction time was replaced with 0.1 hour, the procedure was otherwise the same as in example 1, and a white oily solid product was prepared with a yield of 96%, and the product was characterized by means of a Bruker Avance type superconducting fourier digital nmr spectrometer with the following characterization data:1H NMR(400MHz,CDCl3)δ7.82(dd,J＝8.4,1.3Hz,2H),7.63–7.58(m,1H),7.45(ddd,J＝16.7,8.1,4.1Hz,3H),7.37–7.27(m,3H),3.89(t,J＝6.2Hz,2H),2.95(t,J＝6.2Hz,2H).13C NMR(101MHz,CDCl3)δ198.91,139.04,138.53,137.60,133.46,131.05,131.00,130.62,129.43,128.46,125.64,63.97,36.30.
example 4
Taking the preparation of 2-hydroxyethyl benzophenone compound of the following formula as an example, the raw materials and the preparation method thereof are as follows:
Figure BDA0002771317410000071
in example 4, the trifluoromethanesulfonic acid used in example 1 was replaced with equimolar p-toluenesulfonic acid, the solvent was replaced with benzene, the reaction time was replaced with 12 hours, the other steps were the same as in example 1, and a white oily solid product was prepared with a yield of 82%, and the product was characterized by Bruker Avance type superconducting fourier digital nmr spectroscopy with the following characterization data:1H NMR(400MHz,CDCl3)δ7.82(dd,J＝8.4,1.3Hz,2H),7.63–7.58(m,1H),7.45(ddd,J＝16.7,8.1,4.1Hz,3H),7.37–7.27(m,3H),3.89(t,J＝6.2Hz,2H),2.95(t,J＝6.2Hz,2H).13C NMR(101MHz,CDCl3)δ198.91,139.04,138.53,137.60,133.46,131.05,131.00,130.62,129.43,128.46,125.64,63.97,36.30.
example 5
Taking the preparation of 2-hydroxyethyl benzophenone compound of the following formula as an example, the raw materials and the preparation method thereof are as follows:
Figure BDA0002771317410000072
in example 5, the triflic acid used in example 1 was replaced with trifluoroacetic acid, the amount of acid was replaced with 2 times the amount of the substance of triflic acid, the solvent was replaced with acetonitrile, the reaction time was replaced with 12 hours, the other steps were the same as in example 1, and a white oily solid product was prepared with a yield of 58%, and the obtained product was characterized by means of a Bruker Avance type superconducting fourier digital nuclear magnetic resonance spectrometer with the following data:1H NMR(400MHz,CDCl3)δ7.82(dd,J＝8.4,1.3Hz,2H),7.63–7.58(m,1H),7.45(ddd,J＝16.7,8.1,4.1Hz,3H),7.37–7.27(m,3H),3.89(t,J＝6.2Hz,2H),2.95(t,J＝6.2Hz,2H).13C NMR(101MHz,CDCl3)δ198.91,139.04,138.53,137.60,133.46,131.05,131.00,130.62,129.43,128.46,125.64,63.97,36.30.
example 6
Taking the preparation of 2-hydroxyethyl phenyl p-chlorobenzophenone of the following formula as an example, the raw materials and the preparation method are as follows:
Figure BDA0002771317410000081
in example 6, the 1-phenylisochroman used in example 1 was replaced with equimolar 1-p-chlorophenylisochroman and the other procedure was the same as in example 1 to prepare a white solid product with 83% yield and characterized by the following data:1H NMR(400MHz,CDCl3)δ7.75(d,J＝8.6Hz,2H),7.51–7.47(m,1H),7.43(d,J＝8.7Hz,3H),7.33–7.26(m,2H),3.85(t,J＝6.3Hz,2H),2.92(t,J＝6.2Hz,2H).13C NMR(101MHz,CDCl3)δ197.59,140.03,139.05,138.09,135.95,131.94,131.19,129.22,128.83,128.20,125.75,63.88,36.26.
example 7
Taking the preparation of the compound 2-hydroxyethyl-phenyl-m-toluketone as an example, the raw materials and the preparation method thereof are as follows:
Figure BDA0002771317410000082
in example 7, the 1-phenylisochroman used in example 1 was replaced with equimolar 1-m-tolyl isochroman and the other steps were the same as in example 1 to prepare the product as a white solid in 86% yield as characterized by:1H NMR(400MHz,CDCl3)δ7.66(s,1H),7.58(d,J＝7.6Hz,1H),7.48(dd,J＝7.2,1.4Hz,1H),7.42(d,J＝7.2Hz,2H),7.35(dd,J＝10.0,4.5Hz,2H),7.32–7.26(m,1H),3.89(t,J＝6.2Hz,2H),2.95(t,J＝6.2Hz,2H),2.41(s,3H).13C NMR(101MHz,CDCl3)δ199.16,139.02,138.69,138.38,137.61,134.31,131.01,130.95,130.92,129.43,128.33,128.09,125.63,63.99,36.30,21.34.
example 8
Taking the preparation of the compound 2-hydroxyethyl phenyl propiophenone with the following formula as an example, the raw materials and the preparation method are as follows:
Figure BDA0002771317410000091
in example 8, the 1-phenylisochroman used in example 1 was replaced with equimolar 1-phenylethylisochroman and the other steps were the same as in example 1 to prepare the product as a white solid in 75% yield as characterized by:1H NMR(400MHz,CDCl3)δ7.63(d,J＝7.9Hz,1H),7.40(dd,J＝7.6,1.2Hz,1H),7.29(t,J＝7.7Hz,5H),7.23(d,J＝7.0Hz,2H),3.88(t,J＝6.9Hz,2H),3.15(t,J＝7.6Hz,2H),2.88(t,J＝6.9Hz,2H),3.05(t,J＝7.6Hz,2H).13C NMR(101MHz,CDCl3)δ203.08,141.07,138.06,137.81,132.10,131.40,128.76,128.55,128.42,126.68,126.18,63.92,36.26,33.26,30.30.
example 9
Taking the preparation of 2-hydroxyethyl-4, 5-dimethoxy benzophenone as an example, the raw materials and the preparation method thereof are as follows:
Figure BDA0002771317410000101
in example 9, the 1-phenylisochroman used in example 1 was replaced with equimolar 1-phenyl-6, 7-dimethoxyisochroman and the other steps were the same as in example 1 to prepare the product as a white solid in 91% yield and characterized by the following:1H NMR(400MHz,CDCl3)δ7.84(d,J＝7.5Hz,2H),7.61(d,J＝6.9Hz,1H),7.50(t,J＝6.9Hz,2H),6.90(d,J＝12.8Hz,2H),3.98(s,3H),3.93–3.89(m,2H),3.79(s,3H),2.95(t,J＝5.1Hz,2H).13C NMR(101MHz,CDCl3)δ198.01,151.47,146.34,138.14,133.88,133.19,130.59,130.41,128.42,113.48,113.42,64.11,56.17,56.05,36.08.
example 10
Taking the preparation of 2-hydroxyethyl-4, 5-dimethoxy phenyl p-toluketone compound as an example, the raw materials and the preparation method are as follows:
Figure BDA0002771317410000102
in example 10, the 1-phenylisochroman used in example 1 was replaced with equimolar 1-p-tolyl-6, 7-dimethoxyisochroman and the other steps were the same as in example 1 to prepare the product as a white solid in 92% yield as characterized by:1H NMR(400MHz,CDCl3)δ7.65(d,J＝8.2Hz,2H),7.20(d,J＝7.2Hz,2H),6.80(s,1H),6.78(s,1H),3.89(s,3H),3.82(t,J＝5.9Hz,2H),3.70(s,3H),2.84(t,J＝6.1Hz,2H),2.37(s,3H).13C NMR(101MHz,CDCl3)δ197.72,151.29,146.30,144.19,135.45,133.58,130.79,130.71,129.14,113.39,113.24,64.07,56.14,56.03,36.03,21.71.
example 11
Taking the preparation of 2-hydroxyethyl-4, 5-dimethoxy phenyl p-nitro benzophenone as an example, the raw materials and the preparation method are as follows:
Figure BDA0002771317410000111
in example 11, the 1-phenylisochroman used in example 1 was replaced with equimolar 1-p-nitrophenyl-6, 7-dimethoxyisochroman and the other procedure was the same as in example 1 to prepare a yellow solid in 78% yield as characterized by:1H NMR(400MHz,CDCl3)δ8.01(d,J＝8.8Hz,2H),7.81(d,J＝8.8Hz,2H),6.97(s,1H),6.85(s,1H),3.96(d,J＝5.8Hz,2H),3.93(s,3H),3.74(s,3H),3.03(t,J＝6.1Hz,2H).13C NMR(101MHz,CDCl3)δ195.88,151.73,150.07,146.84,143.70,132.88,130.92,128.95,123.60,114.18,113.49,64.09,56.21,56.13,36.17.
example 12
Taking the preparation of 2-hydroxyethyl-4, 5-dimethoxyphenyl cyclohexyl ketone as an example, the raw materials and the preparation method thereof are as follows:
Figure BDA0002771317410000112
in example 12, the 1-phenylisochroman used in example 1 was replaced with equimolar 1-cyclohexyl-6, 7-dimethoxyisochroman and the other steps were the same as in example 1 to prepare the product as a white oily solid in 77% yield as characterized by:1H NMR(400MHz,CDCl3)δ7.12(s,1H),6.76(s,1H),3.92(s,3H),3.91(s,3H),3.86(t,J＝7.0Hz,2H),2.93(m,1H),2.87(t,J＝7.0Hz,2H),1.84(t,J＝13.3Hz,4H),1.71(d,J＝10.7Hz,1H),1.50–1.18(m,5H).13C NMR(101MHz,CDCl3)δ206.35,151.00,147.02,132.08,130.37,114.51,111.80,63.33,56.25,55.96,36.36,33.12,29.25,25.92,25.84.
example 13
Taking the preparation of the compound 2-hydroxyethyl-4, 5-dimethoxy phenyl p-methoxy phenyl ketene as an example, the raw materials and the preparation method thereof are as follows:
Figure BDA0002771317410000121
in example 14, the 1-phenylisochroman used in example 1 was replaced with equimolar 1-p-methoxystyryl-6, 7-dimethoxyisochroman, and the other procedure was identical to example 1, a white solid was prepared with a yield of 70%, and the product obtained was characterized by means of a Bruker Avance type superconducting Fourier digital nuclear magnetic resonance spectrometer with the following characterization data:1H NMR(400MHz,CDCl3)δ7.57(dd,J＝16.6,12.4Hz,3H),7.08(t,J＝7.9Hz,2H),6.93(d,J＝8.7Hz,2H),6.84(s,1H),3.94(s,3H),3.92(d,J＝3.4Hz,2H),3.89(s,3H),3.85(s,3H),2.96(t,J＝5.9Hz,2H).13C NMR(101MHz,CDCl3)δ193.97,160.95,150.49,145.80,145.11,132.56,130.83,129.35,126.21,122.70,113.51,112.61,111.03,63.10,55.29,55.00,54.43,35.09.

Claims (6)

1. method for preparing 2-hydroxyethyl phenyl ketone by catalytic oxidation of isochromanThe method is characterized in that: 1-substituted isochroman of formula (1) and
Figure FDA0002771317400000013
dissolving acid in an organic solvent, uniformly mixing, or dissolving 1-substituted isochroman as shown in formula (1) and an aryl carbocation compound in an organic solvent, uniformly mixing, reacting at a preset temperature, and separating to obtain 2-hydroxyethyl phenyl ketone as shown in formula (2);
Figure FDA0002771317400000011
wherein A is Ar or R, Ar is any one of phenyl, naphthyl, p-tolyl, o-tolyl, m-tolyl, p-tert-butylphenyl, p-chlorophenyl, p-bromophenyl, p-fluorophenyl, p-nitrophenyl, p-methoxyphenyl, p-trifluoromethylphenyl, m-chlorophenyl and m-nitrophenyl, and R is any one of C1-C6 alkyl, cycloalkyl, styryl, p-toluenyl, p-chlorostyryl and p-nitrobenzylyl; b and C are H or OCH respectively3。
2. The process for preparing 2-hydroxyethyl phenyl ketone by catalytic oxidation of isochroman according to claim 1, wherein: said
Figure FDA0002771317400000014
The acid is any one of C1-C8 alkyl sulfonic acid, perfluoroalkyl sulfonic acid, aryl sulfonic acid, camphor sulfonic acid, squaric acid, trifluoroacetic acid and picric acid.
3. The process for preparing 2-hydroxyethyl phenyl ketone by catalytic oxidation of isochroman according to claim 1, wherein: the aryl carbonium ion compound is any one of triphenylmethyl tetrafluoroborate, triphenylhexachloroantimonate and triphenylmethyl perchlorate.
4. Root of herbaceous plantThe process for preparing 2-hydroxyethyl phenyl ketone by catalytic oxidation of isochroman according to claim 1, wherein: said 1-substituted isochroman and
Figure FDA0002771317400000012
the molar ratio of the acid or the 1-substituted isochroman to the aryl carbenium ion compound is 1 (1-2).
5. The process for preparing 2-hydroxyethyl phenyl ketone by catalytic oxidation of isochroman according to claim 1, wherein: the organic solvent is any one of dichloroethane, methane chloride, chloroform, dichloromethane, carbon tetrachloride, acetonitrile, dioxane, tetrahydrofuran, ethyl acetate, cyclohexane, benzene, toluene and xylene.
6. The process for preparing 2-hydroxyethyl phenyl ketone by catalytic oxidation of isochroman according to claim 1, wherein: the reaction temperature is 25-80 ℃, and the reaction time is 0.1-12 hours.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6482819B1 (en) * 1997-07-31 2002-11-19 Gyogyszerkutato Intezet Kft. 2,3-benzodiazepine derivatives
US20030092705A1 (en) * 2001-01-22 2003-05-15 Schering Corporation Treatment of malaria with farnesyl protein transferase inhibitors

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6482819B1 (en) * 1997-07-31 2002-11-19 Gyogyszerkutato Intezet Kft. 2,3-benzodiazepine derivatives
US20030092705A1 (en) * 2001-01-22 2003-05-15 Schering Corporation Treatment of malaria with farnesyl protein transferase inhibitors

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