“…The organic phase was dried (Na 2 SO 4 ), concentrated under reduced pressure, and chromatographed on silica gel with CH 2 Cl 2 f 4% Et 2 O/CH 2 Cl 2 (R f = 0.24 in 10% Et 2 O/CH 2 Cl 2 ) to afford, after solvent removal, syringyl acetate (0.613 g, 3.12 mmol, 50%) and desired compound 2 (1.08 g), which was recrystallized from ethanol to yield colorless crystals (0. 13 C NMR (ppm, CDCl 3 ) δ: 170.8 (CdO), 170.6 (CdO), 169.6 (CdO), 169.5 (CdO), 153.3 (C 2,6 ), 134.6 (C 1 ), 124.9 (C 4 ), 105.6 (C 3,5 ), 101.5 (C 1 0 ), 73.2 (C 3 0 ), 72.1 (C 2 0 ), 72.0 (C 5 0 ), 68.6 (C 4 0 ), 62.4 (C 6 0 ), 56.4 (2 Â ArOCH 3 ), 20.9 (COCH 3 ), 20.83 (2 Â COCH 3 ), 20.78 (COCH 3 ). ESI-HRMS (m/z): Calcd for C 22 H 28 NaO 12 þ ([M þ Na] þ ), 507.1478; found, 507.1498.…”