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Preparation method of 1-indanone and derivative thereof

A kind of derivative, indanone technology, applied in the field of preparation of 1-indanone and its derivatives, can solve the problems of low solid acid yield, a large amount of waste acid and the like, and achieves convenient recycling, convenient operation and high yield. Effect

Active Publication Date: 2019-04-26
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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Problems solved by technology

[0004] The purpose of the present invention is to provide a preparation method of 1-indanone and derivatives thereof, which solves the problems of a large amount of waste acid produced by using protonic acid in the prior art, and the low yield of solid acid, and can be passed through a one-pot reaction. , efficient and convenient synthesis of 1-indanone and its derivatives

Method used

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  • Preparation method of 1-indanone and derivative thereof
  • Preparation method of 1-indanone and derivative thereof
  • Preparation method of 1-indanone and derivative thereof

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[0022] A preparation method of 1-indanone and derivatives thereof, the method comprising:

[0023] React phenylpropionic acid and its derivatives, heteropolyacids, and phase-transfer catalysts with the structure shown in formula (1) in an aprotic, non-polar organic solvent at a reaction temperature of 60-150°C, and undergo a dehydration acylation reaction , the reaction solvent is separated from the heteropolyacid and the phase transfer catalyst, the reaction solvent is concentrated to separate out 1-indanone and its derivatives, and the separated heteropolyacid and phase transfer catalyst are recycled, which can continue to catalyze the next pot reaction without deactivation .

[0024]

[0025] Among them, R 1 , R 2 and R 3 are each independently H, alkyl or alkoxy.

[0026] Further, the above R 1 , R 2 and R 3 are each independently H, Me or OMe.

[0027] The above-mentioned aprotic and non-polar organic solvents include any one or two or more of petroleum ether (...

Embodiment 1

[0035] Dissolve 0.6g (4mmol) of phenylpropionic acid in 15mL of cyclohexane, add 1.15g (0.4mmol) of phosphotungstic acid and 0.064g (0.2mmol) of tetrabutylammonium bromide, heat and stir at 90°C under heterogeneous conditions, Reflux for 2 hours, filter with suction, remove cyclohexane, the residue solidified and precipitated white crystals of 1-indanone, the yield was higher than 96%; m.p.41-43 ° C; 1H-NMR (CDCl 3 , 400MHz): δ7.31-7.35(m, 2H), 7.21-7.25(m, 2H), 2.99(t, J=6.0Hz, 2H); 2.71(t, J=6.0Hz, 2H).

Embodiment 2

[0037] Dissolve 0.66g (4mmol) of 4-methylphenylpropionic acid in 15mL petroleum ether, add 1.15g (0.4mmol) of phosphotungstic acid and 0.045g (0.2mmol) of benzyltriethylammonium chloride, under heterogeneous conditions Heated and stirred at 120°C and refluxed for 2 hours, filtered with suction to remove petroleum ether, the residue solidified and precipitated white crystals of 6-methylindanone, the yield was higher than 95%; m.p.62-64°C; 1H-NMR (CDCl 3 ,300MHz):δ7.56(s,1H),7.35-7.42(m,2H),3.10(t,J=6.0Hz,2H); 2.69(t,J=6.0Hz,2H),2.40(s, 3H).

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Abstract

The invention discloses a preparation method of 1-indanone and a derivative thereof. The preparation method comprises the steps that phenylpropionic acid with the structure shown as the formula (1), aderivative of the phenylpropionic acid, heteropolyacid and a phase transfer catalyst are subjected to a one-pot reaction in an aprotic non-polar organic solvent, the reaction temperature is 60-150 DEG C, and the 1-indanone and the derivative thereof are obtained through dehydration acylation, wherein in the formula (1), R1, R2 and R3 are each independently H, alkyl or alkoxy. According to the preparation method, the 1-indanone and the derivative thereof can be conveniently prepared through a one-pot method, an intermolecular reaction is avoided, and the selectivity and the yield are high. (Please see the specifications for the formula).

Description

technical field [0001] The invention relates to a preparation method of indanone, in particular to a preparation method of 1-indanone and derivatives thereof. Background technique [0002] Indenone ring structure exists in many natural products, synthetic drugs, pesticides and other molecules. In the synthesis of biologically active compounds, indanone has strong industrial application prospects as a synthetic raw material. There are also applications in synthesis. [0003] The main synthetic method of 1-indanone is through 3-arylpropionyl chloride or 3-arylpropionic acid via protonic acid H 2 SO 4 , HF, trifluoromethanesulfonic acid and other catalyzed intramolecular Friedel-Crafts acylation reactions. In these synthesis methods, a large amount of waste acid will inevitably be produced. Although it has been reported to use solid acid Nafion-H (polymeric perfluoroalkanesulfonic acid) instead of protonic acid and Lewis acid to catalyze intramolecular acylation to prepare 1...

Claims

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Application Information

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IPC IPC(8): C07C45/45C07C49/67
CPCC07C45/455C07C2602/08C07C49/67
Inventor 胡晓允
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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