The autocatalytic kinetic was explained by a reaction involving the acid-catalyzed enolization of the key intermediate, propanoyl chloride, as a rate-determining step.
First, propanoic anhydride conducted initiation (Scheme 1; see (2)) and formed propanoyl chloride.
The two possible acidic degradation products are (2-(6-methoxynaphthalen-2-yl) propanoyl
)glycine ([R.sub.t] = 2.4 min) and naproxen ([R.sub.t] = 3.6 min) (illustrated in Figure 5).
Synthesis of (2S)-(methanesulfonyloxy) Propanoyl
Chloride, a Key Intermediate in the Asymmetric Synthesis of Naproxen.
Propanoic acid (6.7x10-5 mmol) and dry thionyl chloride (8.2x 10-5mmo l) were reacted to s ynthes ize propanoyl
The reactions of 4 with methyl iodide, benzyl chloride, acetyl chloride, benzoyl chloride, 4-methoxybenzoyl chloride, 2-chlorobenzoyl chloride, propanoyl
chloride, 2-bromoethanol and chloroacetyl chloride were studied.