A facile synthesis of α,α′-bis(substituted benzylidene) cycloalkanones catalyzed by p-TSA under solvent-free conditions

Figures & data

Scheme 1.  Synthesis of α,α′-bis(substituted benzylidene) cycloalkanones

Table 1. Preparation of α,α′-bis(substituted benzylidene) cycloalkanone catalyzed by p-TSA at 80°C under solvent-free conditions.

						Mp (°C)
Entry	Cycloalkanone	Ar	Product	Time (min)	Yield (%) (a)	Found	Reported (Ref.)
1		C6H5		20	75	116–118	116–118 22
2		4-ClC6H4		10	98	146–148	146–148 14
3		3-NO2C6H4		5	84	188–190	188–189 12
4		4-MeOC6H4		5	75	160–162	160–162 23
5		4-MeC6H4		5	80	167–169	168 24
6		3-FC6H4		15	80	88–89	88–89 25
7		4-NO2C6H4		5	82	203–204	159–160 26
8		2,4-Cl2C6H3		10	86	163–164	163–164 11
9		C6H5		5	90	188–189	188–189 27
10		4-ClC6H4		5	85	229–230	229–230 14
11		4-MeOC6H4		5	80	214–216	214–216 14
12		4-MeC6H4		10	85	243–244	243–244 11
13		4-NO2C6H4		5	86	253–254	230–231 12
14		3-FC6H4		5	80	190–193	88–89 25
15		C6H5		20	87	97–99	97–99 27
16		4-ClC6H4		5	90	156–160	156–160 27
17		3-NO2C6H4		15	85	165–166	– (b)
18		3-FC6H4		15	88	98–99	– (b)
19		4-MeOC6H4		5	85	137–139	137–139 27
20		4-MeC6H4		10	85	125–127	125–127 27
Note: (a) Isolated yields, (b) not reported.

Table 2. Comparison of results using p-TSA with other heterogeneous catalyst for synthesis of α,α'-bis(substituted benzylidene) cycloalkanones.

Entry	Catalyst	T (°C)	Time (h)	Yield (%)	Ref.
1	copper(II) trifluoroacetate	90	6	77–99	1
2	Cu(OTf)2	80	6–12	86–96	12
3	Silica sulfuric acid	80	2–3.5	86–97	24
4	KF/Al2O3	35–40	0.5–2.5	60–96	23
5	Sulfonated Carbon Nanocage	70	0.5–2	72–92	26
6	p-TSA	80	5–20 min	75–98	This work

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