4'-Hydroxyacetophenone → HCID 19892555, compound

Participants

Reaction Conditions

Reaction Steps

p-Hydroxyacetophenone (40g, 294 mmol) was charged into a reactor containing acidified isoamyl alcohol (200 mL, acidified with anhydrous HCl). Isoamyl nitrite (79 ml, 69g, 588 mmol) was added slowly to maintain a temperature of 25° C. Reaction was monitored by HPLC. At the end of the reaction, ethyl acetate (500 ml) was added and the reaction mixture was transferred to a separator funnel. The organic layer was washed with water (2 ×250 ml), saturated NaHCO3 (1×250 ml) and brine (1×250 ml). The organic solution was dried over MgSO4 and distilled under reduced pressure to remove solvents. Chromatography over silica gel with CH2Cl2 yielded, after removal of solvent, 56.5 g of product (183 mmol, 62% yield). The product was confirmed by mass spectroscopy and nmr. [1H-nmr(200 MHz, acetone-d6); δ 0.93 (m, 12 H, CH3), 1.4 (m, 4 H, C--CH2 -- C), 1.7 (m, 2H, --CH--), 3.5 and 3.8 (m, 4 h, --OCH2), 5.1 (s, lH, O--CH--O), 0), 6.9, 8.0 (dd, 2 H each, aromatic), and 9.3 (broad s, 1 H phenolic H); 13C-nmr (50 MHz, acetone -d6) δ22.7, 22.8 (CH3), 25.6, 39.4 (CH2 --CH--), 67.0 (CH2 -O), 105.1 (O--CH--O), 115.8, 126.9, 133.1, 163 (aromatic), 192.8 (C=O); MS (direct probe) m/z 308 (M+), 187, 121, 71 (100)].

Provenance & Evidence