Fig. 2: Optimization of the reaction conditions.
From: Synthesis of valuable benzenoid aromatics from bioderived feedstock
a, Reaction of DOH and 1a. b, Solvent. Reaction conditions: DOH (0.1 mmol), 1a (2.0 equiv), solvent (0.5 ml), r.t., overnight. c, Additives. Reaction conditions: DOH (0.1 mmol), 1a (2.0 equiv), THF (0.5 ml), additives (1.0 equiv), r.t., overnight. a66 °C; b1,4-dioxane (0.5 ml), 101 °C. d, Amount of 1a with HOAc (1.0 equiv) as catalyst. Reaction conditions: 1st step: 1a, THF (0.2 ml), HOAc (1.0 equiv), r.t., 5 min; 2nd step: DOH (0.1 mmol), THF (0.3 ml), 66 °C, overnight. e, Amount of HOAc. Reaction conditions: 1st step: 1a (6.0 equiv), THF (0.2 ml), HOAc, r.t., 5 min; 2nd step: DOH (0.1 mmol), THF (0.3 ml), 66 °C, overnight. f, Amount of 1a with TFA (1.0 equiv) as catalyst. Reaction conditions: DOH (0.1 mmol), THF (0.5 ml), 1a, TFA (1.0 equiv), 66 °C, overnight. g, Comparison of reaction in THF and 1,4-dioxane. Reaction conditions: DOH (0.1 mmol), solvent (0.5 ml), 1a (6.0 equiv), TFA (1.0 equiv), 66 °C (101 °C using 1,4-dioxane as solvent), overnight.
