Diethyl Ether → Methyl 3-benzyloxy-1,2-dioxocyclohexa-3,5-diene-5-benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of orthochloranii (1.97 g, 8.02 mmol) in 5 mL of Et2O cooled to −30° C. was added dropwise via an addition funnel over 6 h a solution of methyl 3-benzyloxy-4,5-dihydroxybenzoate (2.0 g, 7.3 mmol) in 115 mL of Et2O. The reaction was stirred for a further 0.5 h at −30° C. and then stored at −20° C. for 20 h. The precipitated red solid was collected by filtration, washed with cold Et2O and dried on a vacuum pump to afford 1.11 g (55%) of the orthoquinone. IR (CDCl3) 1727, 1671 cm−1; 1H NMR (CDCl3, 300 MHz) δ 7.41-7.26 (m. 5H), 6.74 (s. 1H), 6.73 (s, 1H1, 6.56 (s. 2H), 3.92 (s, 3H); 13C NMR (CDCl3, 75 MHz) δ 179.9, 174.2, 164.7, 152.1, 141.3, 134.3, 128.8, 128.7, 127.7, 124.4, 107.7, 71.1, 53.4; MS (−FAB) 272 (M−, 12). Anal. Calc for C15H12O5; C. 66.18; H. 4.41; Found: C, 65.75; H. 4.45.

Provenance & Evidence