Resorcinol → HCID 19982786, compound

Participants

Reaction Steps

A 1 L 3-neck flask fitted with a stir-bar, addition funnel, and an Ar inlet was charged with resorcinol (20.0 g, 182 mmol) and DMF (400 mL). To the resultant solution was added NaH (4.82 g, 200 mmol) in two portions, 10 min apart. The mixture stirred at rt 30 min. 1-Bromo-2-methylpropane (37.4 g, 273 mmol) was then added, and the mixture was heated at 80° C. overnight. The mixture was cooled, diluted with EtOAc (300 mL), and washed with H2O (2×250 mL). The aqueous phases were back-extracted with EtOAc (2×100 mL). The combined organic phases were then diluted with hexanes (500 mL) and washed with half-saturated aqueous NaHCO3 (6×200 mL). The solution was filtered through phase separation paper and concentrated in vacuo to give 13.4 g of 71 as a yellow oil containing 27% dialkylated material as determined by HPLC. The substance was carried on as is. HPLC analysis (5:10:85 H2O:A1:MeOH) showed a purity of 68% with a retention time of 3.9 min and 27% dialkylated material with a retention time of 12.0 min.

Provenance & Evidence