Sodium Chloride → HCID 59643034, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3-[1,3]Dioxan-2-yl-4,5-dimethoxy-phenyl)-p-tolyl-methanol (2.13 g, 6.18 mmol) in 75 mL THF, 56 mL 8N H2SO4 was added and the resulting solution was stirred 2 h at 50° C. After addition of 50 mL saturated NaCl-solution the mixture was extracted with EtOAc (3×50 mL). The pooled organic fractions were washed with saturated NaHCO3-solution (50 mL), then saturated NaCl-solution (50 mL) before being dried over MgSO4 and evaporated under reduced pressure to yield the desired product as a colorless oil. This crude product (2 g) was added to a mixture of 45 mL t-BuOH, 24 mL of a 1.25M K2HPO4-solution and 37 mL of a IM KMnO4-solution and stirred 45 min. at 60° C. The mixture was partitioned between 100 mL saturated NaCl-solution and 100 mL CHCl3 and the aqueous phase was extracted with CHCl3 (3×100 mL). The pooled organic fractions were extracted with 2N NaOH-solution (3×100 mL), then the combined aqueous fractions were acidified with conc. HCl and extracted with CHCl3 (4×100 mL). The organic fractions were pooled, dried over MgSO4 and evaporated in vacuo to yield the title compound as a colorless solid.

Provenance & Evidence