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. 2025 Feb 18;90(8):2915–2926. doi: 10.1021/acs.joc.4c02616

Table 3. Scope of Aldehydes (1 mmol scale) in CTAB 2% and Tween 80 2% for 24 ha.

            Yield(%)b
Entry Aldehyde X W Z T(°C) CTAB Tween 80
1 H CH CH - 25 3a 65 4a 10 3a 84 4a 0
2 4-AcNH CH CH - 25 3b 79 4b 0 3b 85 4b 0
3 4-CH3 CH CH - 25 3c 80 4c 8 3c 78 4c 0
4 4-OCH3 CH CH - 25 3d 82 4d 9 3d 34 4d 0
5 4-OCH3 CH CH - 45 3d - 4d - 3d 66 4d 0
6 2-OCH3 CH CH - 25 3e 59 4e 0 3e 40 4e 0
7 2,6-diOCH3 CH CH - 25 3f 90 4f 0 3f 59 4f 0
8 2,6-diOCH3 CH CH - 45 3f - 4f - 3f 93 4f 0
9 4-OHc CH CH - 25 3g 37 4g 0 3g 27 4g 0
10 4-OHc CH CH - 45 3g 39 4g 0 3g 21 4g 0
11 4-Br CH CH - 25 3h 82 4h 0 3h 30 4h 0
12 4-Br CH CH - 45 3h - 4h - 3h 90 4h 0
14 3-Br CH CH - 25 3i 90 4i 0 3i 76 4i 0
15 2-Br CH CH - 25 3j 55 4j 12 3j 68 4j 0
16 2-Br CH CH - 45 3j 53 4j 19 3j 84 4j 0
16 4-NO2 CH CH - 25 3k 69 4k 12 3k 87 4k 0
17 4-NO2 CH CH - 45 3k 73 4k 15 3k - 4k -
18 4-CN CH CH - 25 3l 66 4m 0 3m 98 4m 0
19 4-COOH CH CH - 25 3m 70 4l 0 3l 0 4l 0
20 4-COOCH3 CH CH - 25 3n 28d 4n 0 3n 11 4n 0
21 - CH N - 25 3o 0 4o 23 3o 8 4o 21
22 - N CH - 25 3p 14 4p 2 3p 47 4p 10
23 - - - S 25 3q 83 4q 12 3q 69 4q 0
24 - - - O 25 3r 54 4r 0 3r 49 4r 0
25 - - - NH 25 3s 31 4s 0 3s 71 4s 0
a

Reaction conditions: 5 mL vial, benzaldehyde (1 mmol), acetophenone (1 mmol), NaOH (1 equiv), surfactant solution (1 mL), rt or 45 °C, 24 h.

b

Isolated yield.

c

2 equiv of NaOH were used.

d

29% of the derivative acid was also isolated.