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. 2023 Sep 1;88(18):12914–12923. doi: 10.1021/acs.joc.3c00757

Table 1. Synthesis of Cyclohexenones in Water.

Entry Synthesis of Conditionsa Yield (%) (anti:syn)
1 1b H2O, 135 °C 96 (64:36)
2 13 H2O, 135 °C 98 (72:28)
3 14 H2O, 135 °C 98 (75:25)
4 15 H2O, 135 °C 90 (15a:15b 67:33), no syn products
5 12 H2O, 135 °C 83 (62:38)
6 1b H2O, RTc 96 (1A, 100:0)
7 1b Brine,d 135 °C 94 (95:5)
a

Reaction conditions: α-ketoacid (2.0 mmol), benzaldehyde (2.0 mmol), ketone (2.0 mmol), NaOH (3 mmol, 10 M at H2O solution), H2O (3 mL); microwave vial was heated to 135 °C and heat was maintained for 30 min.

b

4-Phenyl-3-buten-2-one (2 mmol) is used instead of benzaldehyde and ketone.

c

Reaction was stirred for 4 h at room temperature at 20 mL vial.

d

Brine solution (3 mL, saturated NaCl solution) was used instead of Milli-Q H2O.