A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanones
Abstract
:1. Introduction
2. Results and Discussion
2.1. α,α'-bis-(Substitutedbenzylidene)cycloalkanones
Entry | NaOH (mol%) [a] | Time (min.) | Yield [b] |
---|---|---|---|
1 | 100 | 5 | 99 |
2 | 80 | 5 | 99 |
3 | 40 | 5 | 98 |
4 | 20 | 5 | 98 |
5 | 10 | 5 | 95 |
6 | 1 | 5 | 70 |
Entry | Catalysts | Time | Yield [a] (%) |
---|---|---|---|
[a] Isolated yields which are not optimized. | |||
1 | NaOH (20 mmol), mortar and pestle | 5 min | 98 |
2 | KOH (20 mmol), mortar and pestle | 5 min | 85 |
3 | NaOH (20 mmol), r.t, EtOH | 24 h | 40 |
4 | NaOH (20 mmol), r.t, EtOH | 96 h | 60 |
5 | NaOH (20 mmol), r.t, EtOH | 5 d | 66 |
6 | NaOH (20 mmol), reflux , EtOH | 8 h | 93 |
7 | NaOAc (20 mmol), AcOH, 120 °C | 8 h | 81–93[74] |
8 | NH4OAc (4 mmol), AcOH, 120 °C | 8 h | 83–95[75] |
| ||||
---|---|---|---|---|
Entry | R | n | Yield (%) | mp (°C) (lit.value) [references] |
3a | H | 0 | 98 | 188, (188–190) [ 74], (188–189) [38] |
3b | 2-Br | 0 | 96 | 165, (163–165) [ 74], (162–163) [40] |
3c | 4-Me | 0 | 98 | 184, (183–184) [ 40] |
3d | 4-OMe | 0 | 98 | 211, (210–211) [ 74], (210–211) [38] |
3e | H | 1 | 98 | 119, (119–120) [ 74], (117–118) [38] |
3f | 2-NO2 | 1 | 98 | 159, (158–159) [ 74], (158–159) [74] |
3g | 3-Cl | 1 | 97 | 104, (103–105) [ 74] |
3h | 4-Me | 1 | 98 | 168, (165–167) [ 74], (170.1) [76] |
2.2. Reaction of Acetone (5) with Benzaldehyde (2a)
Molar ratio | Conversion(%) | Yield [a] (%) | ||
---|---|---|---|---|
5 | 2a | 6 | 7 | |
10 mmol | 20 mmol | 100 b | 53 | 42 |
Excess (>5 equiv.) | 10 mmol | 100 b | trace | 96 |
10 mmol | Excess (>3 equiv.) | 100 c | 98 | 0 |
2.3. Reaction of 1,7,7-Trimethyl[2,2,1]hexan-2-one (Camphor, 8) with Substituted-benzaldehyde (2a and 2c)
3. Experimental
3.1. General
3.2. Chemistry
3.2.1. General Procedure for the Preparation of α,α'-bis-(Substituted-benzylidene)cycloalkanones 3a–h
3.2.2. General Procedure for the Preparation of 3i, 3j and 4
3.2.3. Procedure for the Preparation of (1E,4E)-1,5-Diphenylpenta-1,4-dien-3-one (6) and (E)-4-Phenylbut-3-en-2-one (7)
3.2.4. Preparation of (E)-3-Substitutedbenzylidene-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (9)
4. Conclusions
References and Notes
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Rahman, A.F.M.M.; Ali, R.; Jahng, Y.; Kadi, A.A. A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanones. Molecules 2012, 17, 571-583. https://doi.org/10.3390/molecules17010571
Rahman AFMM, Ali R, Jahng Y, Kadi AA. A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanones. Molecules. 2012; 17(1):571-583. https://doi.org/10.3390/molecules17010571
Chicago/Turabian StyleRahman, A. F. M. Motiur, Roushown Ali, Yurngdong Jahng, and Adnan A. Kadi. 2012. "A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanones" Molecules 17, no. 1: 571-583. https://doi.org/10.3390/molecules17010571