Sodium Carbonate → Propionic acid, 2,2-diethoxy-, ethyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl pyruvate (13.92 g, 0.120 moles), triethyl orthoformate (19.44 g, 0.131 moles), ethyl alcohol (9.0 g), and p-toluenesulfonic acid monohydrate (0.0432 g, 0.00227 moles) was stirred at 45° C. overnight under nitrogen atmosphere. Next, after cooling to room temperature, Na2CO3 (1.20 g) was added and the mixture was stirred for 15 minutes. The reaction mixture was then filtered and ethyl alcohol and residual triethyl orthoformate were distilled off under reduced pressure. The residue was subjected to fractional vacuum distillation giving 18.2 g of pure ethyl pyruvate diethyl ketal. NMR (d6-DMSO): 1.27 ppm (t, —CH3, ethyl (ketal), 6H) 1.34 ppm (t, —CH3, ethyl (ester), 3H), 1.40 ppm (s, —CH3—C—COO—, 3H), 3.45 ppm (q, —OCH2CH3, (ketal), 4H), 4.29 ppm (q, —OCH2CH3, (ester), 2H).

Provenance & Evidence