CN104341280A - Method for preparing aldehyde and ketone through alcohol oxidation - Google Patents

Method for preparing aldehyde and ketone through alcohol oxidation Download PDF

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CN104341280A
CN104341280A CN201310317585.5A CN201310317585A CN104341280A CN 104341280 A CN104341280 A CN 104341280A CN 201310317585 A CN201310317585 A CN 201310317585A CN 104341280 A CN104341280 A CN 104341280A
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alcohol
reaction
accordance
ketone
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高爽
李军
王连月
吕迎
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Dalian Institute of Chemical Physics of CAS
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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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
    • C07C45/38—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a primary hydroxyl group
    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
    • C07C45/39—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a secondary hydroxyl group
    • 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
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

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  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention provides a method for preparing aldehyde and ketone through alcohol oxidation. The method comprises: adopting 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as a catalyst, adopting iron phthalocyanine (II) as a co-catalyst, adopting oxygen (or air) as an oxidant, and oxidizing an alcohol in an organic solvent to generate aldehyde and ketone. The method has characteristics of mild reaction conditions, simple operation and less pollution, and is a new green environmental protection method for preparing aldehyde and ketone through catalysis oxidation of alcohol.

Description

A kind of method of alcohol oxidation aldehyde processed and ketone
Technical field
The present invention relates to catalyzed oxidation field, be specifically related to a kind of method that aldehyde ketone prepared by catalyzed oxidation alcohol.
Background technology
It is an important reaction in organic synthesis that alcohols selectivity is oxidized to carbonyl compound, and is widely used in laboratory and industrial production, and in fine chemical industry, play a part key.With 2,3-bis-chloro-5,6-dicyan para benzoquinone (DDQ) alcohol is oxidized to aldehyde and ketone is a kind of known method.(see people such as Becker, The Journal of Organic Chemistry, 45 volumes, 1596-1600 page (1980)).But due to DDQ costly, $ 526/mol (see 2009-2010Aldrich catalog), simultaneously due in his structure containing two-CN groups, facile hydrolysis, and produce certain toxicity.Thus limit its use.Consider from the angle of economy and environment close friend, people are finding a kind of method that DDQ circulation can be made to get up always, as shown in Equation 1, namely make the reduzate DDQH of DDQ be oxidized to DDQ with oxygenant thus oxidizing reaction is carried out continuously.Floreancig in 2010 etc. report with MnO 2for oxygenant DDQ is that catalyzer can carry out oxidizing reaction (Organic Letters2010,12, (20), 4686-4689), 2011 effectively, the Mn (OAc) such as Helquist 3for oxygenant, DDQ is catalyst alcohol oxidation aldehyde ketone processed (Organic Letters2011,13, (8), 2071-2073).Although above-mentioned two kinds of methods all successfully achieve DDQ catalytic oxidation, the consumption of DDQ is higher is 20mol%, and the consumption of oxygenant Mn salt is 6 times of substrate.Can produce a large amount of metal-salts after reaction, aftertreatment bothers, and does not meet eco-friendly requirement.
Summary of the invention
The object of the invention is that overcoming above-mentioned oxidation system exists aftertreatment trouble, and the problems such as pollution provide a kind of DDQ catalyzed oxidation alcohol to produce the novel method of aldehyde ketone.The method adopts inexpensive Green Oxidant oxygen or air, reduces production cost, reduces environmental pollution.
For achieving the above object, the technical solution used in the present invention comprises the steps: under liquid reaction condition, in organic solvent, with 2,3-bis-chloro-5,6-dicyan para benzoquinone (DDQ) is catalyzer, and phthalein cyanogen iron (II) is promotor, and oxygen (or air) is oxidized alcohol for oxygenant.The effect of phthalein cyanogen iron (II) is that the reduzate DDQH of DDQ is oxidized to DDQ and oxidizing reaction is carried out by catalytic oxygen.
The structural formula of phthalein cyanogen iron (II) used in the present invention is:
The pressure of oxygen used in the present invention or air is 0.1MPa ~ 1.0MPa.
Organic solvent used in the present invention is methyl alcohol, ethanol, dioxane, methylene dichloride, ethylene dichloride, toluene, acetonitrile, DMF, one or more in N,N-dimethylacetamide.Preferred dioxane and DMF.
The present invention the substrate that is suitable for be aromatic alcohol: wherein R 1, R 2, R 3, R 4, R 5=-H, Ph ,-C nh 2n+1(n=1-10), OR 9(R 9=-H ,-C nh 2n+1(n=1-4)), NR 7r 8(R 7, R 8=-H ,-C nh 2n+1, (n=1-4)), R 6=-H, Ph ,-C nh 2n+1(n=1-4).Vinyl carbinol: wherein R=Ph ,-C nh 2n+1, or be (n=1-10) deng cyclic allylic alcohol.Propargyl alcohol: wherein R=Ph ,-C nh 2n+1(n=1-10), and wherein R, R 1=Ph ,-C nh 2n+1(n=1-10).
The temperature of reaction that the present invention is applicable to typically is about 50 DEG C-150 DEG C.Preferably, this reaction is carried out about 60 DEG C-120 DEG C.
Chloro-5, the 6-dicyan para benzoquinone (DDQ) of catalyzer 2,3-bis-of the present invention and alcohol react with the mol ratio of 0.5:100-15:100.Be preferably 1:100-10:100.The consumption of DDQ is relevant with the activity of substrate, active high substrate, and the consumption of DDQ is less, and the use of active low material DDQ increases to some extent.Chloro-5, the 6-dicyan para benzoquinone (DDQ) of catalyzer 2,3-bis-and promotor phthalein cyanogen iron (II) react with the mol ratio of 100:2-100:100.Be preferably 100:5-100:50.
After reaction terminates, reaction system is cooled to room temperature, then slowly releases oxygen, removal of solvent under reduced pressure, gained mixture is dissolved in methylene dichloride, washing, dry, and removing methylene dichloride, can obtain the high product of purity after column chromatography.
Due to the utilization of above-mentioned technology, the present invention compared with prior art has following advantages:
1. the oxidizing reaction of this catalyst system, uses green inexpensive oxygen (or air) to be oxygen source; Avoid and use prior art toxic and dangerous larger oxygenant, as: Mn (OAc) 3and MnO 2deng, environmentally friendly, and advantage of lower cost.
2., due to oxygen, the use of catalyzer and promotor makes reaction conditions gentle, and selectivity is high, simple to operate, and product is easily separated.
Embodiment
Specific embodiment of the invention step is described in detail below by some embodiments, should by these embodiments as scope of the invention restriction.Synthesis under normal pressure carries out in 500mL round-bottomed flask, and compressive reaction carries out in the 100mL stainless steel cauldron of polytetrafluoro liner.
The investigation of embodiment 1, reaction conditions
First we are that model substrates is investigated reaction conditions with styryl carbinol, and product is phenylacrolein, 1hNMR (300MHz, CDCl 3) δ 9.71 (d, J=7.8Hz, 1H), 7.60-7.52 (m, 3H), 7.47-7.42 (m, 3H), 6.75 (dd, J=15.9,7.8Hz, 1H), 13c NMR (100.6MHz, CDCl 3) δ 128.2,128.3,128.8,131.0,133.7,152.7,193.6.
Type reaction step is as follows: by 13.4g (0.1mol) styryl carbinol, 2.27g (0.01mol) DDQ, 1.137g phthalein cyanogen iron (II), 30mL dioxane joins in 100mL stainless steel cauldron, airtight, exchanges oxygen 3 times, oxygen pressure 0.1Mpa, 95 DEG C are stirred 10h.Decompression removing dioxane, gained mixture is dissolved in methylene dichloride, washing, dry, and removing methylene dichloride, post is separated and obtains 9.7g phenylacrolein (yield 73%).
The results are shown in Table 1
The investigation of table 1 reaction conditions
Table 1 is visible, DDQ, and iron phthalein cyanogen, oxygen three has vital effect to the carrying out of oxidizing reaction, indispensable.The temperature of reaction of system is higher, and pressure is larger, reacts faster.Air can substitute oxygen, but needs larger pressure.Different solvents result has difference, and dioxane and DMF are as well.Embodiment 2, p-Hydroxybenzylalcohol are oxidized
By 124.2g p-Hydroxybenzylalcohol, 22.7g DDQ, 22.73g phthalein cyanogen iron (II), 340mLN, dinethylformamide joins in 500mL reaction flask, airtight, exchanges oxygen 3 times, connects oxygen balloon (0.1Mpa), and 100 DEG C are stirred 13h.Decompression removing DMF, gained mixture is dissolved in methylene dichloride, washing, dry, and removing methylene dichloride, post is separated and obtains 100g(yield: 81%) p-Hydroxybenzaldehyde pale yellow crystals. 1H NMR(400MHz,DMSO):δ6.93(d, 3J H,H=8.8Hz,1H),7.76(d, 3J H,H=8.8Hz,2H),9.78(s,1H),10.58(s,1H); 13C NMR(100.6MHz,DMSO)δ116.0,128.6,132.3,163.5,191.1。
Embodiment 3, benzyl alcohol oxidation
By 10.8g phenylcarbinol, 3.4g DDQ, 4.25g phthalein cyanogen iron (II), 50mL acetonitrile joins in 100mL stainless steel cauldron, under the oxygen pressure of 0.3MPa, 95 DEG C of reaction 16h are cooled to room temperature, slowly release oxygen, decompression removing acetonitrile, gained mixture is dissolved in methylene dichloride, washing, drying, removing methylene dichloride, post is separated and obtains 9g(yield: 84%) phenyl aldehyde. 1H NMR(300MHz,CDCl 3,):δ7.51(t,J=7.6Hz,2H),7.61(t,J=7.2Hz,1H),7.86(d,J=7.6Hz,2H),9.99(s,1H)。 13C NMR(100.6MHz,CDCl 3):δ128.7,129.4,134.1,136.0,192.0。
Embodiment 4, diphenyl-carbinol are oxidized
By 184.2g diphenyl-carbinol, 20.5g DDQ, 39.78g phthalein cyanogen iron (II), 200mL dioxane joins in 500mL reaction flask, passes into oxygen (30mL/min) 100 DEG C reaction 15h, decompression removing dioxane, gained mixture is dissolved in methylene dichloride, washing, dry, removing methylene dichloride, post is separated and obtains 165g(yield: 90%) benzophenone. 1H NMR(300MHz,CDCl 3)δ7.46(m,2H)，7.57(m,2H),7.79(m,2H)。 13C NMR(100.6MHz,CDCl 3)δ128.6,130.5,132.6,139.7,196.4。
Embodiment 5,9-hydroxyphenyl fluorene are oxidized
By 18.2g9-hydroxyphenyl fluorene, 2.27g DDQ, 1.14g phthalein cyanogen iron (II), 50mL acetonitrile joins in 100mL stainless steel cauldron, under the air pressure of 0.5MPa, 95 DEG C of reaction 8h, are cooled to room temperature, slowly deflate, decompression removing acetonitrile, gained mixture is dissolved in methylene dichloride, washing, dry, removing methylene dichloride, post is separated and obtains 12g(yield: 66%) product 9-Fluorenone.Yellow solid, mp78-80 DEG C, 1h NMR (400MHz, CDCl 3): δ 7.27 (d, 3j h,H=7.2Hz, 2H), 7.50-7.44 (m, 4H), 7.64 (d, 3j h,H=7.2Hz, 2H); 13c NMR (100.6MHz, CDCl 3) δ 120.2,124.2,128.9,134.0,134.5,144.3,193.8.
Embodiment 6,2-cyclohexenol are oxidized
By 98.14g2-cyclohexenol, 22.7g DDQ, 28.4g phthalein cyanogen iron (II), 300mL dioxane joins in 500mL reaction flask, pass into bubble oxygen, oxygen flow is 35mL/min, after 100 DEG C of reaction 16h. reaction terminates, removing dioxane, gained mixture adds methylene dichloride and dissolves, and washing is dry, removing methylene dichloride, is separated and obtains 78.5g(yield: 80%) 2-cyclonene. 1H NMR(300MHz,CDCl 3)δ2.02(p,J=6.3Hz,2H),2.38-2.32(m,2H),2.43(t,J=7.2Hz,2H),6.01(d,J=10.2Hz,1H),7.00(dt,J=9.9,4.2Hz,1H)。 13C NMR(100.6MHz,CDCl 3)δ24.8,27.3,38.8,128.2,139.4,198.7。
Embodiment 7, the oxidation of ethanol of 4-methoxyl group-a-methylbenzene
By 152g4-methoxyl group-a-methylbenzene ethanol, 11.35g DDQ, 11.36g phthalein cyanogen iron (II), 350mLN, dinethylformamide joins in 500mL reaction flask, passes into air bubbling, air velocity is 25mL/min, 95 DEG C of reaction 36h. remove DMF, and gained mixture adds methylene dichloride and dissolves, washing, drying, removing methylene dichloride, post is separated and obtains 100g(yield: 66%) 4-methoxyl group-a-methyl acetophenone. 1H NMR(400MHz,CDCl 3):δ2.47(s,3H),3.78(s,3H),6.85(d, 3J H,H=8.4Hz,2H),7.85(d, 3J H,H=8.4Hz,2H); 13C NMR(100.6MHz,CDCl 3)δ26.1,55.2,113.5,130.1,130.4,163.3,196.6。
Embodiment 8,1-phenyl-2-propine-1-alcohol are oxidized
By 13.2g1-phenyl-2-propine-1-alcohol, 2.72g DDQ, 3.42g phthalein cyanogen iron (II), 20mL ethylene dichloride joins in 100mL reactor, and under the air pressure of 0.8MPa, 85 DEG C of reaction 12h, are cooled to room temperature, washing, drying, removing ethylene dichloride, post is separated and obtains 9.0g(yield: 69%) 1-phenyl-2-propine-1-ketone.Yellow solid fusing point 42.5-43.5 DEG C; 1h NMR (300MHz, CDCl 3) δ 3.45 (s, 1H), 7.49 (t, J=7.4Hz, 2H), 7.63 (t, J=7.4Hz, 1H), 8.16 (d, J=7.4Hz, 2H), 13c NMR (100.6MHz, CDCl 3) δ 80.2,80.7,128.7,129.6,134.5,136.1,177.3.
Embodiment 9,3,4,5-trimethoxybenzyl alcohol is oxidized
By 198.22g3,4,5-trimethoxybenzyl alcohol, 15.89gDDQ, 19.89g phthalein cyanogen iron (II), 250mL acetonitrile, airtight, connect air balloon, 85 DEG C of reaction 15h. remove acetonitrile, gained mixture adds methylene dichloride and dissolves, and washing is dry, removing methylene dichloride, post is separated and obtains 189g(yield: 95%) 3,4,5-trimethoxybenzyl alcohol, white is to micro-yellow needle-like crystals.Fusing point 74-75 DEG C, 1h NMR (400MHz, CDCl 3): δ 3.92 (s, 6H), 3.93 (s, 3H) 7.12 (s, 2H), 9.86 (s, 1H), 13c NMR (100.6MHz, CDCl 3) δ 56.2,61.0,106.7,131.7,153.6,191.0.
Embodiment 10,3-phenyl-2-propine-1-alcohol are oxidized
By 132.16g3-phenyl-2-propine-1-alcohol, 22.7gDDQ, 45.46g phthalein cyanogen iron (II), 200mL dioxane, airtight, connect air balloon, 105 DEG C of reaction 20h. remove dioxane, gained mixture adds methylene dichloride and dissolves, and washing is dry, removing methylene dichloride, post is separated and obtains 105g phenyl-allylene aldehyde (yield 79%), yellow liquid 1h NMR (400MHz, CDCl 3): δ 7.36 (t, 3j h,H=7.6Hz, 2H), 7.45 (t, 3j h,H=8.0Hz, 1H), 7.57 (d, 3j h,H=7.2Hz, 2H), 9.38 (s, 1H), 13c NMR (100.6MHz, CDCl 3) δ 88.3,95.1,119.2,128.6,131.2,133.1,176.8.
Embodiment 11,1,3-phenylbenzene-2-propine-1-alcohol is oxidized
By 104.13g1,3-phenylbenzene-2-propine-1-alcohol, 17.1gDDQ, 8.56g phthalein cyanogen iron (II), 300mL dioxane, joins in 500mL reaction flask, airtight, connect air balloon, 102 DEG C of reaction 20h. remove dioxane, gained mixture adds methylene dichloride and dissolves, washing, dry, removing methylene dichloride, post is separated and obtains 80g phenyl-allylene aldehyde (yield 77%), yellow liquid. 1H NMR(400MHz,CDCl 3):δ7.39(t,J=7.6Hz,2H),7.51-7.43(m,3H),7.60(t,J=7.6Hz,1H),7.66(d,J=7.2Hz,2H),9.38(s,1H)， 13C NMR(100.6MHz,CDCl 3)δ86.8,93.0,119.9,128.5,128.6,129.4,130.7,132.9,134.0,136.7,177.8。

Claims (7)

1. the method for an alcohol oxidation aldehyde processed and ketone, the method comprises the steps: under liquid phase state condition, in organic solvent, with 2,3-bis-chloro-5,6-dicyan para benzoquinone (DDQ) is catalyzer, and phthalein cyanogen iron (II) is promotor, and to be oxygenant carry out oxidizing reaction to alcohol obtains one in aldehyde and ketone or two kinds for a kind of in oxygen or air or two kinds;
Wherein 2,3-bis-chloro-5,6-dicyan para benzoquinone and alcohol react with the mol ratio of 0.5:100 ~ 15:100;
Chloro-5, the 6-dicyan para benzoquinone of 2,3-bis-and phthalein cyanogen iron (II) react with the mol ratio of 100:2 ~ 100:100.
2. in accordance with the method for claim 1, it is characterized in that:
The structural formula of described phthalein cyanogen iron (II) is:
3. in accordance with the method for claim 1, it is characterized in that: described temperature of reaction is 50 DEG C-150 DEG C.
4. in accordance with the method for claim 1, it is characterized in that: the organic solvent reacting used is methyl alcohol, ethanol, dioxane, methylene dichloride, ethylene dichloride, toluene, acetonitrile, DMF, one or two or more kinds in N,N-dimethylacetamide.
5. in accordance with the method for claim 1, it is characterized in that: a kind of or two kinds the pressure in oxygen or air is 0.1Mpa ~ 1.0MPa.
6. in accordance with the method for claim 1, it is characterized in that: the substrate alcohol that is suitable for be one or two or more kinds in following alcohol;
The substrate alcohol that is suitable for be aromatic alcohol: wherein R 1, R 2, R 3, R 4, R 5difference=-H, Ph ,-C nh 2n+1(n=1-10) ,-OR 9(R 9=-H or-C nh 2n+1(n=1-4)) ,-NR 7r 8(-R 7, R 8difference=-H or-C nh 2n+1(n=1-4)), R 6=-H, Ph or-C nh 2n+1(n=1-4);
Or be vinyl carbinol: wherein R=Ph ,-C nh 2n+1, or be (n=1-10) deng cyclic allylic alcohol;
Or be propargyl alcohol: wherein R=Ph ,-C nh 2n+1, or be (n=1-10) wherein R, R 1difference=Ph or-C nh 2n+1(n=1-10).
7. in accordance with the method for claim 1, it is characterized in that: the volumetric molar concentration of reaction substrate is 0.1-1.0 mol/L.
CN201310317585.5A 2013-07-25 2013-07-25 Method for preparing aldehyde and ketone through alcohol oxidation Pending CN104341280A (en)

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CN105884574A (en) * 2016-05-12 2016-08-24 浙江工业大学 Method for removing p-methoxyl benzyl protective group of hydroxyl
CN105884574B (en) * 2016-05-12 2018-04-13 浙江工业大学 A kind of method to methoxy-benzyl protection group of eliminating hydroxide
WO2019232715A1 (en) * 2018-06-06 2019-12-12 Rhodia Operations Selective oxidation of alcohols

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