Molly Binder

Chem 122L
Wintergreen Lab

Objective: The purpose of this lab was to convert aspirin into wintergreen through the reflux
process. The progress of the reaction was checked periodically using TLC plates to check the
sample against commercial oil of wintergreen. A sample of product was then analyzed via 1H
NMR analysis.

Figure 1: Aspirin to wintergreen reaction. Image taken from lab manual.

Data/Results:
TLC results after 30 minutes: Percentage (%)
Wintergreen: ~80%
Sample: ~70%
TLC results after 60 minutes:
Wintergreen ~80%
Sample ~80%
Table 1: TLC plate data. Rf values were approximated.

% yield = mass product / mass reagent x 100

% yield = 1.06g wintergreen / 1.625g aspirin x 100 = 65.23% yield

Discussion:
The reflux process converted aspirin into wintergreen in this experiment. The conversion
process was monitored throughout using TLC plate analysis and it was shown that the
conversion was complete after 60 minutes. The NMR analysis then determined if there were any
impurities in the final product. It showed… The low 65.23% yield could be due to sources of
error. For example, when the aspirin was crushed using the mortar and pestle some of the
powdery aspirin was stuck in the mortar and was not transferred to the round bottom flask. The
impurities in the wintergreen NMR could be due to the roto vap purification process not being
carried out to completion.