Acetic Acid → HCID 59595154, compound

Participants

Reaction Steps

Prepared according to general procedure A using tert-butyl 3-(2-hydroxyphenyl)-3-oxopropanoate (18) (354 mg, 1.5 mmol), p-tolualdehyde (150 μL, 1.5 mmol), 15.0 mL benzene, piperidine (15 μL, 0.15 mmol) and glacial acetic acid (8.6 μL, 0.15 mmol), refluxed for 3 h. Purified via recrystallization from hexanes/CH2Cl2, yielding 350 mg (69%) of clear prisms. mp=86-89° C.; IR (film) 2978.2; 1712.8; 1624.5; 1155.2 cm−1; 1H NMR (100.7 MHz, CDCl3) δ 11.93 (bs, 1H), 7.82 (s, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.48 (t, J=8.2 Hz, 1H), 7.25-7.08 (AA′BB′, 4H), 7.03 (d, J=8.2 Hz, 1H), 6.81 (t, J=7.6 Hz, 1H), 2.30 (s, 3H), 1.40 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 202.0, 163.9, 162.8, 142.3, 141.3, 137.1, 131.9, 130.4 (x2), 130.1, 129.9, 120.2, 119.5, 118.4, 82.6, 28.1, 21.6; LRMS (electrospray): Mass calculated for C21H22O4, [M]+, 338.14. Found [M+23]+, 361.4.

Provenance & Evidence