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. 2021 Jan 25;6(6):4313–4328. doi: 10.1021/acsomega.0c05563

Table 3. Summary of Kinetic Reaction Profiles Derived from Solvent Screening Studiesa.

entry solvent t (h)b 4b yield (%) dehydration: 4c + 4d + 4e yield (%) carbon mass balance (%) cis–trans ratio 4b
1 water 0.5 49 40 89 64:36
2 MeOH 0.75 46 34 80 65:35
3 EtOH 0.75 56 36 92 67:33
4 n-PrOH 1.5 61 28 89 67:33
5 i-PrOH 2 69 27 96 71:29
6 n-BuOH 1 36 53 89 69:33
7 i-BuOH 3 61 25 86 68:32
8 s-BuOH 3 72 22 94 67:33
9 t-BuOH 3 74 21 95 67:33
10 EtOAc 4 62 37 99 69:31
11 CPME 2 62 36 98 69:31
12 THF 7 65 31 96 71:29
13 dioxane 2 69 29 98 68:32
14c toluene 7 26 73 99 71:29
15c heptane 7 29 69 98 52:48
a

Reaction conditions: 50 mmol of 4 and 5.1 wt % Ru/C, 100 °C, 50 bar H2.

b

Specific reaction time upon which complete conversion was observed via GC-FID.

c

The reaction was run for 7 h without collection of kinetic samples. Since the diol products emulsified out of the solvent, the entire reaction mixture was dissolved in acetonitrile for GC analysis.