1. In a reflux apparatus (p 496 (3rd ed) 572 (2nd ed)) place 1 gram of salicylic acid and 3 ml of methanol. Mix the reagents by swirling. Carefully add 1 ml of concentrated sulfuric acid mixing by swirling after each drop. Take note of any temperature changes. A white precipitate may form. Attach the condenser if you have not already done so.

2. Add a boiling stone to the flask and reflux for 1 hour or until you see the mixture get cloudy as a second layer forms. My reaction seemed to take 1.25 hours.

3. Allow the mixture to cool to room temperature. (IMPORTANT!) Extract the methanol mixture twice with methylene chloride. (CH2Cl2 is not miscible with methanol.)

4. Combine the CH2Cl2 extractions in either a very large test tube or a small erleneyer. Carefully wash the extracts with 3 ml of a 5% NaHCO3 solution. THERE WILL BE SOME H2SO4 in the CH2Cl2.

5. Wash the product containing solution with saturated NaCl (or at least 1M NaCl).

6. Dry product over Na2SO4. Filter. Remove solvent under reduced pressure.

7. Check purity using TLC and refractive index. Find % yield.

Prelab.

1. This lab involves 2 extractions and three washes. Make a flow chart showing where your product is at each step. Why do we do each of these extractions/washes. (p135 or 136 has an example of a flowchart.)

2. What is the organic chemistry definition of extraction and wash? What is the difference between the two?

3. Prepare your notebook to take data (see page 21 if you are unsure of what is required). Remember to look up the FW of both the reactants and the products. Look up the boiling points of the solvents. Look up the refractive index of the product.