Formaldehyde → Methyl Palmoxirate

Participants

Reaction Steps

Lithium hydride (0.32 g, 0.040 m), paraformaldehyde (0.16 g, 0.0053 m), and methanol (0.32 g, 0.010 m) were heated together in 25 ml DMF at 30°-40° C. After 1 hour, methyl α-chloropalmitate (3.05 g, 0.010 m) was added; the remaining paraformaldehyde (0.16 g, 0.0053 m) was added in two portions. The reaction was worked up after 51/2 hours of heating. The reaction mixture was extracted with hexane; the hexane was washed with water and dried over Na2SO4. The mixture was filtered and stripped to a crystalline residue. The residue was recrystallized from methanol to give 2.49 g (83.5%) yield of methyl tetradecylglycidate (m.p. 47°-48° C., glc purity>99%).

Provenance & Evidence