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 |
Reaction conditions: 5 mL vial, benzaldehyde (1 mmol), acetophenone (1 mmol), NaOH (1 equiv), surfactant solution (1 mL), rt or 45 °C, 24 h.
Isolated yield.
2 equiv of NaOH were used.
29% of the derivative acid was also isolated.