CN106748693B - A kind of synthetic method of alpha-hydroxyacetone compounds - Google Patents
A kind of synthetic method of alpha-hydroxyacetone compounds Download PDFInfo
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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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Abstract
The invention discloses a kind of synthetic methods of alpha-hydroxyacetone compounds.The prior art uses precious metals complex, organic phosphorus compound or elemental iodine as catalyst, expensive, recycling higher cost mostly；Alkali uses complicated organic base or cesium carbonate is this expensive and uncommon inorganic base；Solvent uses highly polar aprotic solvent mostly, and post-processing is complicated, it is difficult to realize industrial applications.The present invention uses common inorganic low price sulfur-containing compound for catalyst, and under alkali and aerobic conditions, catalysis of carbonyl chemical combination object, which reacts, is made alpha-hydroxyacetone compounds.The raw material that the present invention uses is easy to get, cheap, and high income, and product purity is high, and waste discharge amount is few and is easily processed, it is easy to accomplish industrialization.
Description
Technical field
The invention belongs to chemosynthesis technical field, specifically a kind of cheap, efficient alpha-hydroxyacetone compounds
Synthetic method.
Background technique
Alpha-hydroxyacetone compounds are a kind of extremely important and widely used compounds.It, which can be used as, has biology living
The natural products and medicine intermediate of property, also can be used as the photoinitiator in ultraviolet-curing paint.Meanwhile alpha-alcohol ketone structure
Widely used synthon in unit or organic synthesis.Hydroxyl can be used as the groups temperature such as double bond, ester group, carbonyl, halogenated hydrocarbons
The reacting precursor of sum.Carbonyl can be used as the reacting precursor of the groups such as hydroxyl, amino, alkyl.In addition, alpha-hydroxyacetone compounds are also
It can derive and turn to heterocyclic compound.Therefore, alpha-hydroxyacetone compounds are a kind of compounds with significant application value.α-hydroxyl
The synthesis of base ketone structural unit has great research significance.
The synthetic method of alpha-hydroxyacetone compounds reported in the literature is more.Wherein, benzoic conden-sation reaction is a classics
Reaction.However, can only obtain the alpha-hydroxyacetone compounds with specific structure by the reaction, use scope is smaller.Absolutely
Most of alpha-hydroxyacetone compounds can not be obtained by benzoic conden-sation reaction.
Other synthetic methods can be divided mainly into direct synthesis technique and indirect synthesis technique.Direct synthesis technique passes through with ketone
Conjunction object is raw material, is realized by the hydroxylating of c h bond.Indirect synthesis technique is first converted into enol by ketone compounds
Then oxidation reaction occurs for salt, silyl enol ether, enol acetate or alkyl enol ether to realize.Indirect synthesis technique can also
Alpha-halogenate reaction occurs by ketone compounds, reaction is hydrolyzed then to realize.Indirect synthesis technique process is complicated, can not
The more waste of the generation avoided.And direct synthesis technique has the advantages that simple, efficient, waste is few, is current people's research
Emphasis.
Direct synthesis technique passes through oxygen (air) oxidation generally to realize.Seek suitable reaction condition, is especially catalyzed
The selection of agent, alkali and solvent is always the emphasis of research.
Document (J.Am.Chem.Soc., 2011,133,1760-1762) reports one kind with double-core Pd (II) compound
Catalyst, 1,3,4,6,7,8- hexahydro -2H- pyrimido [1,2-a] pyrimidine (hppH) are used as ligand, and oxygen is high as oxidant
The 'alpha '-hydroxylation reaction for realizing ketone compounds of chemo-selective and regioselectivity.However, the double-core that this method uses
Pd (II) compound, hppH are that structure is complicated, preparation is difficult, expensive raw material, are not suitable for industrialized production.
CN201310514007.0 reports one kind using organic phosphorus (III) compound as catalyst, cesium carbonate as alkali,
DMSO is as solvent, the method for efficiently synthesizing alpha-hydroxyacetone compounds.However, this method have the shortcomings that it is more: (1) use
DMSO is high boiling solvent, and difficult solvent recovery, product separation process is more complex after reaction, and higher cost.(2) cesium carbonate
Price is very expensive.(3) organic phosphorus (III) compound catalyst of the 1-2 equivalent used becomes organic phosphorus (V) after the completion of reaction
Compound.Organic phosphorus (V) compound separates difficulty with DMSO, and has to pass through reduction reaction after separating and become organic phosphorus
(III) compound could reuse, and cost recovery is very high.A large amount of phosphorous waste can be generated if not recycling,
Cause environmental issue.
CN201410142396.3 reports a kind of synthetic method, using sodium carbonate as alkali, diisopropylethylamine, diiodo-
Change the mixture of samarium and ferrocene as auxiliary agent, bromination isopropyl triphenyl phosphine is synthesized as additive, DMSO as solvent
Alpha-hydroxyacetone compounds.This method also has the shortcomings that more: (1) use DMSO as solvent, the separation of product is difficult after reaction,
And it is at high cost.(2) reaction system is complicated, has used multiple compounds as auxiliary agent and additive.(3) reagent used, such as two
Means of samarium iodide, bromination isopropyl triphenyl phosphine are expensive, and recycling is difficult.
CN201510033064.6 report it is a kind of using elemental iodine or N- bromo-succinimide (NBS) as being catalyzed
Agent, method of the dimethyl sulfoxide as oxidant, source of hydroxyl groups and solvent synthesis alpha-hydroxyacetone compounds.This method equally has DMSO
As the problem that solvent bank comes, and use elemental iodine or NBS as catalyst, it is expensive, and recycling difficulty.
In conclusion direct synthesis technique is typically chosen oxygen as oxidant, due to the more difficult activation of oxygen, in order to reach compared with
Good yield, the prior art use noble metal (such as Pd) complex, organic phosphorus (III) compound or elemental iodine conduct mostly
Catalyst, it is expensive, recycle higher cost；Alkali uses complicated organic base or this price of cesium carbonate
Expensive and uncommon inorganic base；Solvent uses highly polar aprotic solvent mostly, and post-processing is complicated, it is difficult to realize that industrialization is answered
With.
Summary of the invention
The technical problem to be solved by the present invention is to overcome the problems of the above-mentioned prior art, a kind of reaction condition is provided
Simply, high income, waste discharge amount is few and is easily processed, is easy to industrialized alpha-hydroxyacetone compounds synthetic method.
In order to achieve the above object, the present invention adopts the following technical scheme that: a kind of synthesis side of alpha-hydroxyacetone compounds
Method in organic solvent mixes catalyst with alkali, is added after carbonyls (I) under aerobic conditions and reacts obtained Alpha-hydroxy
Ketone compound (II),
Wherein, R1、R2、R3It is selected from hydrogen, alkyl, alkoxy, amino, aromatic radical, substituted aromatic radical, heterocyclic aromatic base
One of；
Alternatively, R1And R2It combines and naphthenic base or substituted naphthenic base, benzo naphthenic base or substituted benzene is collectively formed
And naphthenic base, indole ring or substituted indole ring, R at this time3Selected from hydrogen, alkyl, alkoxy, amino, aromatic radical, substituted virtue
One of perfume base, heterocyclic aromatic base；
Alternatively, R2And R3It combines and naphthenic base or substituted naphthenic base, benzo naphthenic base or substituted benzene is collectively formed
And naphthenic base, indole ring or substituted indole ring, R at this time1Selected from hydrogen, alkyl, alkoxy, amino, aromatic radical, substituted virtue
One of perfume base, heterocyclic aromatic base；
The catalyst is the mixing of one or more of sodium sulfite, sodium hydrogensulfite, sodium thiosulfate
Object, preferably sodium sulfite.
The alpha-hydroxyacetone compounds are preferred are as follows: 2- hydroxyl -2- phenyl cyclohexanone, 2- hydroxy-2-methyl -1- phenyl third
Ketone, 3- hydroxy-3-methyl -2- butanone, 1- hydroxyl -1,1- diphenyl acetone, 2- hydroxy-2-methyl -1- (2- thiophene) acetone, 2-
Hydroxy-2-methyl -2,3- bihydrogen-1-indenone, (3S, 7R, 7aR) -6- benzyl -7- (1- hydroxyl -2- oxocyclohexyl) -3- phenyl
Tetrahydro -5H- imidazo [1,5-c] [1,3] thiazole -5- ketone.
Further, the alkali is potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, sodium methoxide, sodium ethoxide, isopropyl
Sodium alkoxide, preferably sodium hydroxide.
Further, the organic solvent is methanol, ethyl alcohol, propyl alcohol, isopropanol, the tert-butyl alcohol, preferred alcohol.
Further, the molar ratio of the alpha-hydroxyacetone compounds and catalyst is 1:0.1~5, preferably 1:1~3；
The molar ratio of alpha-hydroxyacetone compounds and alkali is 1:0.1~10, preferably 1:0.1~1.
Further, the reaction temperature of the reaction is 0~100 DEG C, preferably 10-20 DEG C；Reaction pressure be 1~
100atm, preferably 0.5-1.5atm.
Further, the aerobic conditions use air, oxygen or oxygen and nitrogen mixed gas, preferably oxygen.
Synthetic method difference from prior art of the invention is:
1, the present invention uses alcohols as solvent, and alcohols solvent low boiling point is convenient for recycling, and cheap, product point
It is also relatively simple from process.
2, the present invention uses cheap and easily-available sodium hydroxide (potassium) or sodium alkoxide (potassium) as alkali, is advantageously implemented industrialization
Production.
3, the present invention is catalyst using common inorganic low price sulfur-containing compound, and raw material is easy to get, cheap, waste
Discharge amount is few and is easily processed, it is easy to accomplish industrialization.
Specific embodiment
The present invention will be further described With reference to embodiment.
The synthesis of 1 2- hydroxyl -2- phenyl cyclohexanone of embodiment
At 15 DEG C, sodium hydroxide (8g, 0.2mol) and ethyl alcohol (150ml), stirring are added into 250ml three-necked flask
0.5h.It sequentially adds sodium sulfite (25.21g, 0.2mol), 2- phenyl cyclohexanone (34.84g, 0.2mol) meets a 1000ml
The oxygen ball of size stirs lower reaction 6h.
After reaction, the pH of reaction solution is adjusted to 7 with the hydrochloric acid of 2M, vacuum distillation removes ethyl alcohol.Be added 50ml water with
50ml toluene stands liquid separation after stirring, water layer extracts (30ml × 3) with toluene, merges organic phase, uses anhydrous Na2SO4It is dry, mistake
Filter, solvent evaporated obtain yellow solid 33.83g, purity 98%, yield 95.13%.
1H NMR(600MHz,CDCl3) δ 7.40 (d, J=7.7Hz, 2H), 7.33 (t, J=7.9Hz, 1H), 7.28 (d, J
=7.9Hz, 2H), 4.75 (br, 1H), 2.98-3.04 (m, 1H), 2.51-2.56 (m, 1H), 2.39-2.46 (m, 1H), 2.01-
2.06(m,1H),1.65-1.87(m,4H)；13C NMR(150MHz,CDCl3)212.68,140.01,129.10,128.28,
126.34,80.05,38.85,38.82,28.30,23.03.ESI-MS:191.5(M+H)+,189.2(M-H)-。
Embodiment 2-15
The step of repeating embodiment 1, the dosage of immobilized substrate, reaction pressure are constant.Change temperature, the type of alkali and use
Amount, the type and dosage of catalyst, the type of solvent, obtained result are as shown in table 1 below.
The result of 1 embodiment 2-15 of table
The synthesis of 16 2- hydroxy-2-methyl -1- phenylacetone of embodiment
At 15 DEG C, sodium hydroxide (8g, 0.2mol) and ethyl alcohol (150ml), stirring are added into 250ml three-necked flask
0.5h.It sequentially adds sodium sulfite (25.21g, 0.2mol), 2- methyl-1-phenylacetone (29.64g, 0.2mol) connects one
The oxygen ball of 1000ml size stirs lower reaction 6h.
After reaction, the pH of reaction solution is adjusted to 7 with the hydrochloric acid of 2M, vacuum distillation removes ethyl alcohol.Be added 50ml water with
50ml toluene stands liquid separation after stirring, water layer extracts (30ml × 3) with toluene, merges organic phase, uses anhydrous Na2SO4It is dry, mistake
Filter, solvent evaporated obtain light brown oily substance 30.85g, purity 97%, yield 91.13%.
1H NMR(600MHz,CDCl3) δ 8.05 (d, J=7.6Hz, 2H), 7.53 (t, J=7.6Hz, 1H), 7.48 (d, J
=7.5Hz, 2H), 4.15 (br, 1H), 1.65 (s, 6H)；13C NMR(150MHz,CDCl3)204.68,133.65,132.86,
129.52,128.34,76.13,28.33.ESI-MS:165.3(M+H)+,163.2(M-H)-。
The synthesis of 17 3- hydroxy-3-methyl -2- butanone of embodiment
At 15 DEG C, sodium hydroxide (8g, 0.2mol) and ethyl alcohol (150ml), stirring are added into 250ml three-necked flask
0.5h.It sequentially adds sodium sulfite (25.21g, 0.2mol), 3- methyl -2- butanone (17.26g, 0.2mol) connects one
The oxygen ball of 1000ml size stirs lower reaction 6h.
After reaction, the pH of reaction solution is adjusted to 7 with the hydrochloric acid of 2M, vacuum distillation removes ethyl alcohol.Be added 50ml water with
50ml toluene stands liquid separation after stirring, water layer extracts (30ml × 3) with toluene, merges organic phase, uses anhydrous Na2SO4It is dry, mistake
Filter, solvent evaporated obtain colourless liquid 19.74g, purity 98%, yield 94.73%.
1H NMR(600MHz,CDCl3)δ3.98(br,1H),2.23(s,3H),1.39(s,6H)；13C NMR(150MHz,
CDCl3)212.28,75.95,26.30,23.03.ESI-MS:103.6(M+H)+,101.1(M-H)-。
The synthesis of 18 1- hydroxyl -1,1- diphenyl acetone of embodiment
At 15 DEG C, sodium hydroxide (8g, 0.2mol) and ethyl alcohol (150ml), stirring are added into 250ml three-necked flask
0.5h.It sequentially adds sodium sulfite (25.21g, 0.2mol), 1,1- diphenyl acetone (42.05g, 0.2mol) connects one
The oxygen ball of 1000ml size stirs lower reaction 6h.
After reaction, the pH of reaction solution is adjusted to 7 with the hydrochloric acid of 2M, vacuum distillation removes ethyl alcohol.Be added 50ml water with
50ml toluene stands liquid separation after stirring, water layer extracts (30ml × 3) with toluene, merges organic phase, uses anhydrous Na2SO4It is dry, mistake
Filter, solvent evaporated obtain light yellow solid 45.50g, purity 98%, yield 98.54%.
1H NMR(600MHz,CDCl3)δ7.32-7.40(m,10H),4.88(br,1H),2.22(s,3H)；13C NMR
(150MHz,CDCl3)208.58,141.29,128.54,128.13,128.02,85.90,26.22.ESI-MS:227.4(M+
H)+,225.6(M-H)-。
The synthesis of embodiment 19 2- hydroxy-2-methyl -1- (2- thiophene) acetone
At 15 DEG C, sodium hydroxide (8g, 0.2mol) and ethyl alcohol (150ml), stirring are added into 250ml three-necked flask
0.5h.It sequentially adds sodium sulfite (25.21g, 0.2mol), 2- methyl-1-(2- thiophene) acetone (30.85g, 0.2mol) connects
The oxygen ball of one 1000ml size stirs lower reaction 6h.
After reaction, the pH of reaction solution is adjusted to 7 with the hydrochloric acid of 2M, vacuum distillation removes ethyl alcohol.Be added 50ml water with
50ml toluene stands liquid separation after stirring, water layer extracts (30ml × 3) with toluene, merges organic phase, uses anhydrous Na2SO4It is dry, mistake
Filter, solvent evaporated obtain light yellow solid 31.02g, purity 98%, yield 89.28%.
1H NMR(600MHz,CDCl3) δ 7.95 (d, J=3.8Hz, 1H), 7.63 (d, J=5.1Hz, 1H), 7.18 (t, J
=5.1Hz, 1H), 3.48 (br, 1H), 1.69 (s, 6H)；13C NMR(150MHz,CDCl3)196.98,138.85,134.44,
134.32,128.05,75.99,28.31.ESI-MS:171.7(M+H)+,169.3(M-H)-。
The synthesis of 20 2- hydroxy-2-methyl -2,3- bihydrogen-1-indenone of embodiment
At 15 DEG C, sodium hydroxide (8g, 0.2mol) and ethyl alcohol (150ml), stirring are added into 250ml three-necked flask
0.5h.It sequentially adds sodium sulfite (25.21g, 0.2mol), 2- methyl -2,3- bihydrogen-1-indenone (29.24g, 0.2mol) connects
The oxygen ball of one 1000ml size stirs lower reaction 6h.
After reaction, the pH of reaction solution is adjusted to 7 with the hydrochloric acid of 2M, vacuum distillation removes ethyl alcohol.Be added 50ml water with
50ml toluene stands liquid separation after stirring, water layer extracts (30ml × 3) with toluene, merges organic phase, uses anhydrous Na2SO4It is dry, mistake
Filter, solvent evaporated obtain light yellow solid 31.15g, purity 98%, yield 94.10%.
1H NMR(600MHz,CDCl3) δ 7.75 (d, J=7.8Hz, 1H), 7.63 (t, J=7.1Hz, 1H), 7.43 (d, J
=7.1Hz, 1H), 7.38 (t, J=7.7Hz, 1H), 3.25 (d, J=17.2Hz, 1H), 3.21 (d, J=17.2Hz, 1H),
2.98(br,1H),1.49(s,3H)；13C NMR(150MHz,CDCl3)207.98,151.05,135.41,127.82,
126.55,124.85,77.59,42.23,25.51.ESI-MS:163.5(M+H)+,161.2(M-H)-。
Embodiment 21 (3S, 7R, 7aR) -6- benzyl -7- (1- hydroxyl -2- oxocyclohexyl) -3- phenyl tetrahydro -5H- miaow
The synthesis of azoles simultaneously [1,5-c] [1,3] thiazole -5- ketone
At 15 DEG C, sodium hydroxide (8g, 0.2mol) and ethyl alcohol (150ml), stirring are added into 250ml three-necked flask
0.5h.It sequentially adds sodium sulfite (25.21g, 0.2mol), (3S, 7S, 7aR) -6- benzyl -7- (2- oxocyclohexyl) -3- benzene
Base tetrahydro -5H- imidazo [1,5-c] [1,3] thiazole -5- ketone (81.31g, 0.2mol), connects the oxygen of a 1000ml size
Ball stirs lower reaction 6h.
After reaction, the pH of reaction solution is adjusted to 7 with the hydrochloric acid of 2M, vacuum distillation removes ethyl alcohol.Be added 50ml water with
50ml toluene stands liquid separation after stirring, water layer extracts (30ml × 3) with toluene, merges organic phase, uses anhydrous Na2SO4It is dry, mistake
Filter, solvent evaporated obtain white solid 84.68g, purity 98%, yield 97.84%.
1H NMR(600MHz,CDCl3) δ 7.40 (d, J=7.2Hz, 2H), 7.26-7.35 (m, 8H), 6.38 (s, 1H),
5.05 (dd, J=15.6Hz, 1H), 4.40 (dd, J=15.6Hz, 1H), 3.80 (m, 3H), 3.01 (m, 1H), 2.08-2.45
(m,3H),1.89(m,3H),1.63(m,3H)；13C NMR(150MHz,CDCl3)211.52,161.95,141.77,138.41,
128.52,128.41,128.33,127.85,127.66,127.34,125.85,78.94,64.92,61.89,60.33,
47.05,38.23,37.94,34.87,26.81,20.21.ESI-MS:423.3(M+H)+,421.5(M-H)-。
The above described is only a preferred embodiment of the present invention, not making any form to technical solution of the present invention
On limitation.According to the technical essence of the invention any simple modification to the above embodiments, equivalent variations and repair
Decorations, fall within the protection scope of the present invention.
Claims (6)
1. a kind of synthetic method of alpha-hydroxyacetone compounds, which is characterized in that in organic solvent mix catalyst with alkali, add
Obtained alpha-hydroxyacetone compounds (II) is reacted under aerobic conditions after entering carbonyls (I)；
Wherein, R1、R2、R3It is selected from hydrogen, alkyl, alkoxy, amino, aromatic radical, substituted aromatic radical, heteroaromatic
One of base；
Alternatively, R1And R2It combines and naphthenic base or substituted naphthenic base, benzo naphthenic base or substituted benzo ring is collectively formed
Alkyl, indole ring or substituted indole ring, R3Selected from hydrogen, alkyl, alkoxy, amino, aromatic radical, substituted aromatic radical, miscellaneous
One of polycyclic aromatic group；
Alternatively, R2And R3It combines and naphthenic base or substituted naphthenic base, benzo naphthenic base or substituted benzo ring is collectively formed
Alkyl, indole ring or substituted indole ring, R1Selected from hydrogen, alkyl, alkoxy, amino, aromatic radical, substituted aromatic radical, miscellaneous
One of polycyclic aromatic group；
The catalyst is the mixture of one or more of sodium sulfite, sodium hydrogensulfite, sodium thiosulfate；
The alkali is one of potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, sodium methoxide, sodium ethoxide, sodium isopropylate
Or it is two or more；
The organic solvent is one of methanol, ethyl alcohol, propyl alcohol, isopropanol, the tert-butyl alcohol；
The molar ratio of the alpha-hydroxyacetone compounds and catalyst is 1:0.1~5, the molar ratio of alpha-hydroxyacetone compounds and alkali
For 1:0.1~10；
The aerobic conditions use air, oxygen or oxygen and nitrogen mixed gas.
2. synthetic method according to claim 1, which is characterized in that the alkali is sodium hydroxide.
3. synthetic method according to claim 1, which is characterized in that the catalyst is sodium sulfite.
4. synthetic method according to claim 1, which is characterized in that the organic solvent is ethyl alcohol.
5. synthetic method according to claim 1, which is characterized in that the alpha-hydroxyacetone compounds and catalyst rub
, than being 1:1~3, the molar ratio of alpha-hydroxyacetone compounds and alkali is 1:0.1~1 for you.
6. synthetic method according to claim 1, which is characterized in that the reaction temperature of the reaction is 0~100 DEG C, instead
Answering pressure is 1~100atm.
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