4-Methylbenzaldehyde → HCID 54282891, compound

Participants

Reaction Steps

In a fashion similar to that described in Example 3, p-tolualdehyde was condensed with diethyl L-tartrate to provide (4R,5R)-2-(4-methylphenyl)-4,5-dicarboethoxy-1,3-dioxolane, an oil, GLC analysis: 93%, [α]D25 -9.6° (c,0.1,methanol), 1H-NMR (CDCl3)δ7.47 (2H,d,J=8.0 Hz), 7.18 (2H,d,J=8.0 Hz) 6.12 (1H,s), 4.93 (1H,d,J=4.0 Hz), 4.81 (1H,d,J=7.2 Hz), 4.34-4.22 (4H,2 q, overlapping, J=7.2 Hz), 2.34 (3H, s), 1.35-1.26 (6H 2 t, overlapping, J=7.2 Hz). IR (film) 2980, 1740, 1615 cm-1. MS m/e (% abundance) 308(2), 293(1), 279(1), 235(12), 136(68), 119(100), 105(50), 91(20), 77(8), 43(6).

Provenance & Evidence