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. 2020 Mar 3;5(10):5356–5364. doi: 10.1021/acsomega.9b04393

Table 1. Optimization of Reaction Conditions for Hydrolysis of 12 to 14.

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entry solventa time (h) temperature molar ratio 14/15/13b
         
1 0.2 M NaOH 0.5 r.t. 1:0.46:0.16
2 0.2 M NaOH 24 r.t. 1:0.30:0.02
3 0.2 M NaOH 168 r.t. 1:0.27:0
4 1 M NaOH 0.5 r.t. 1:0.20:0.12
5 1 M NaOH 24 r.t. 1:0.12:0.04
6 3 M NaOH 0.5 r.t. 1:0.16:0.10
7 3 M NaOH 24 r.t. 1:0.13:0.04
8 3 M NaOH 72 r.t. 1:0.10:0.04
9 3 M NaOH 168 r.t. 1:0.20:0
10 3 M NaOH 0.5 100 °C 1:0.16:0.06
11 3 M HCl 0.5 r.t. NRc
12 3 M HCl 24 r.t. NRc
13 3 M HCl 3 100 °C 0.07:1:0
a

Reaction conditions: 12 (1.0 mmol), 1,4-dioxane (5 mL), solvent (5 mL), time (0.5–168 h), temperature (room temperature (r.t.) or reflux (100 °C)).

b

Calculated by NMR analysis.

c

NR: no reaction occurred, only 12 detected.