Synthesis of Aspirin Data

I. DATA AND OBSERVATIONS

Table 1. Description of reagents.
Reagents Description Salicylic acid Fine powdery white solid crystals 95% ethanol Clear colorless liquid Acetyl chloride Clear colorless liquid with gas escaping from container FeCl3 Clear colorless liquid Commercial aspirin Fine powdery white solid crystals I2/KI Deep black liquid
KMnO4 Brownish liquid
Phosphoric acid Clear colorless liquid

Table 2. Preparation of Aspirin. Description
Salicylic acid + Acetyl chloride Cloudy white liquid with undissolved white powder
Mixture at room temp White cloudy liquid
Mixture in ice bath White particles settled at the bottom of cloudy white liquid
Suction Filtration
Filtrate White powdery crystals
Residue Clear yellowish liquid
Crude Aspirin White powdery crystals

Table 3. Recrystallization of Aspirin. Description
Crude aspirin + EtOH Clear colorless liquid with undissolved white solids
Mixture during heating Powdery white solids dissolve in clear colorless liquid
Mixture after heating Clear yellowish liquid
Mixture at room temp Clear very pale yellow liquid
Mixture in ice bath White particles started to solidify in very pale yellow liquid
Suction Filtration
Filtrate White needle-like crystals
Residue Cloudy white liquid with slightly undissolved solids
Crude Aspirin White needle-like crystals

Table 4. Recovery Data. Recrystallized Aspirin
Wt. of watchglass + filter paper 53.081g
Wt. of watchglass + filter paper + product 55.995
Weight of product 2.914
Theoretical Yield 2.61g
% Yield 111.65%

Table 5. Melting point determination. Crude Aspirin Recrystallized Aspirin
Melting point 118-130°C 134-136°C
Literature value 135°C 135°C

Table 6. Differentiation of starting materials.
Substance Sol'y in water +/- Fecl3 test +/- KMnO4 +/-
Acetic Chloride Dissolved acetyl chloride. Clear colorless liquid. + Boils upon addition of acetyl chloride. Cloudy yellow solution. --