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A technology of ketone compounds and synthesis methods, which is applied in the field of synthesis of ketone compounds, can solve the problems of application limitations, poor atom economy, cumbersome separation and purification process, etc., and achieve the goal of improving atom economy, avoiding resource waste, and avoiding environmental pollution Effect
Active Publication Date: 2015-12-16
HENAN NORMAL UNIV
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The disadvantages of this method are: 1) It needs to go through multi-step synthesis and tedious separation and purification process; 2) The reaction needs to be carried out under strict anhydrous and oxygen-free conditions, and the conditions are harsh; 3) In addition to aldehyde compound substrates, It is also necessary to use compounds with functional groups such as organic halides as raw materials, which has poor atom economy and low efficiency
The existence of these problems makes the application of the above method in actual production limited.
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Embodiment 1
[0011]
[0012] Add benzaldehyde ( 1a ,0.5mmol,53mg), cyclohexane ( 2a , 10mL) and di-tert-butyl peroxide (TBP, 2mmol, 380uL), then the pressure tube was sealed and placed in a microwave reactor, and the reaction was stirred at 180°C for 1 hour under microwave radiation. After the reaction is over, unreacted 2a , and the residue was separated through a silica gel column (petroleum ether / ethyl acetate=100 / 1) to obtain the product 3a (54.5mg, 58%). The characterization data of this compound are as follows: 1 HNMR (400MHz, CDCl 3 )δ:1.27-1.56(m,5H),1.74-1.77(m,1H),1.84-1.92(m,4H),3.28(tt, J 1 =11.2Hz, J 2 =3.2Hz,1H),7.47(t, J =7.6Hz,2H),7.54-7.58(m,1H),7.95-7.97(m,2H). 13 CNMR (100MHz, CDCl 3 )δ: 25.9, 26.0, 29.4, 45.6, 128.3, 128.6, 132.7, 136.4, 203.9. MS: m / z211[MNa] + .
Embodiment 2
[0014] Add benzaldehyde ( 1a ,0.5mmol,53mg), cyclohexane ( 2a , 10mL) and di-tert-butyl peroxide (TBP, 1mmol, 190uL), then the pressure-resistant tube was sealed and placed in a microwave reactor, and stirred and reacted at 180°C for 1 hour under microwave radiation. After the reaction is over, unreacted 2a , and the residue was separated through a silica gel column (petroleum ether / ethyl acetate=100 / 1) to obtain the product 3a (42.3 mg, 45%).
Embodiment 3
[0016] Add benzaldehyde ( 1a ,0.5mmol,53mg), cyclohexane ( 2a , 10mL) and di-tert-butyl peroxide (TBP, 3mmol, 570uL), then the pressure-resistant tube was sealed and placed in a microwave reactor, and reacted at 180°C for 1 hour under microwave radiation. After the reaction is over, unreacted 2a , and the residue was separated through a silica gel column (petroleum ether / ethyl acetate=100 / 1) to obtain the product 3a (51.7 mg, 55%).
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Abstract
The invention discloses a method for synthesizing a ketone compound. The method comprises the following steps: mixing or dissolving an aldehyde compound and cycloparaffin in an organic solvent; and under the condition of microwave radiation, reacting at 140-180 DEG C in the presence of a free radical initiator, thereby preparing a target product, namely, the ketone compound. The reaction equation of the method is as shown in the specification, wherein R1 is phenyl or substituted phenyl, and the substituent group on the substituted phenyl benzene ring is one or more of fluorine, chlorine, bromine, methyl, methoxyl, trifluoromethyl or hydroxyl. The substituent group is in the ortho-position, meta-position or para-position on the benzene ring, n is an integer within 1-4, the free radical initiator is benzoyl peroxide, di-tert-butyl peroxide or dicumyl peroxide, and the organic solvent is alkane or phenyl. The method for synthesizing the ketone compound has the advantages that the raw material are cheap and easy to obtain, the atom economy is good, the substrate application range is wide, and the like; and the method is applicable to industrial production.
Description
technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of ketone compounds. Background technique [0002] Organic ketones are one of the most important organic compounds. They not only widely exist in various natural products, but also have good biological activities. On the other hand, the carbonyl and α-methylene groups in organic ketones have very rich reactivity and can be used as intermediates for the synthesis of various functional organic molecules. At present, the synthesis of ketones is mainly through the nucleophilic addition of organometallic reagents and aldehydes to obtain alcohol intermediates, and then the corresponding ketones are oxidized. The disadvantages of this method are: 1) It needs to go through multi-step synthesis and tedious separation and purification process; 2) The reaction needs to be carried out under strict anhydrous and oxygen-free conditions, and the conditi...
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