Toluene → HCID 18509354, compound

Participants

Reaction Steps

A 2000 ml three-necked round-bottom flask, equipped with a magnetic stirrer, nitrogen device, thermometer, dropping funnel and a reflux condenser was charged with 591.0 g of crude methyl 3-acetoxy-2-pentyl-2-cyclopentene-1-acetate and 70 g of toluene. At 26° C. 386.9 g (2.04 mol) 40% peracetic acid were added dropwise over a 5.3 h period. Stirring was continued for 2 h. 22.0 g (0.12 mol) of 40% peracetic acid were added over 30 min, and stirring was continued for another 2 h. 350 g of water were added and the water-layer (590.4 g) was separated. Three more washes were made with each 350 ml of water. The organic phase (1273.9 g) was evaporated to give 437.8 g of crude product which was vacuum distilled (0.4 hPa) to furnish 2 fractions, of which the first one (Bp=90-144° C.) was 172.55 g, containing 26.5% of product and the second one was 187.6 g, containing 95% of lactone. 1H-NMR: 0.88 (br t, J=6.7 Hz, Me); 1.15-1.45 (m, 6H); 1.67-1.87 (m, 3H); 2.14-2.63 of overlapping m, 4H); 2.84-2.97 (m, 2H). 13C-NMR: 13.9 (Me), 22.4, 22.6, 25.0, 31.9, 33.0, 35.7, 35.8 (CH2), 38.6 (CH), 89.0 (C), 175.0 (CO2), 210.9 (CO). MS: M+=210 (5): 154 (16), 139 (22), 112 (25), 111 (73), 99 (79), 98 (100), 83 (26), 71 (26), 55 (73), 43 (28).

Provenance & Evidence