Benzoic Acid → Benzyl Benzoate

Participants

Reaction Conditions

Reaction Steps

A mixture comprising benzoic acid (2.45 g, 20 millimoles, Aldrich, 99%), sodium hydroxide (1.90 g, 22.5 millimoles, 50% w/w solution in water, Aldrich) and water (247.2 g) was stirred magnetically at room temperature for about two hours until the solids dissolved in water. The excess molar concentration of sodium hydroxide was 0.125. Next, the aqueous phase was transferred to a three-necked 500 mL flask and warmed up to 45° C. The organic phase consisting of benzyl chloride (7.60 g, 60 millimoles, Aldrich, 97%), 3-methylanisole (GC standard, 0.616 g, 5 millimoles, Aldrich, 99%), and Adogen 464 (0.905 g, 2 millimoles, Aldrich) was added to the aqueous phase and the two phase system was stirred mechanically (600 rpm, a calibrated photo-tachometer) for three hours at 45° C. The organic phase:aqueous phase weight ratio was 1:27. The aliquot, taken after 180 minutes after the addition of the organic phase, was briefly centrifuged, the phases were separated and the organic phase was injected into the GC instrument. The yield of benzyl benzoate based on the limiting reactant (benzoic acid) was 87%. Benzyl Benzoate was accompanied by a small quantity of benzyl alcohol (less than 5%).

Provenance & Evidence