Question

Day 1:

1. What is Oil wintergreen? Name the plant source for Oil of Wintergreen.
2. Draw the structure of the major component in Oil of Wintergreen.
3. Mention three biological activities of Oil of winter green.
4. Using REAXYS tool, find a synthetic protocol for the synthesis of ether derivative of Oil of Winter green.
5. List the starting materials and their quantities required to prepare the given ether derivative.
6. Write the mechanism involved in the proposed reaction.
7. Document the search including screen shots / pictures and submit for grading.

Answer 1

Answer:

1.

Wintergreen oil is a pale yellow or pinkish fluid liquid that's strongly aromatic with sweet, woody odor (components: methyl salicylate (about 98%), α-pinene, myrcene, delta-3-carene, limonene, 3,7-guaiadiene, & delta-cadinene) that gives such plants distinctive "medicinal" smell whenever bruised.

This oil comes from a big plant source of methyl salicylate – wintergreen plants. Easily distilled from plant leaves, oil of wintergreen is 96-99% methyl salicylate & very pungent. Besides smelling minty, methyl salicylate also tastes minty, but wintergreens aren’t mints. These plants are members of the genus Gaultheria, while mint plants like peppermint & spearmint, are of the genus Mentha.

2. Methyl Salicylate:

3.

Wintergreen oil acts in a similar way as aspirin in that it can produce analgesic effect when topically applied on skin. It also shows antipyretic actions when the essence of wintergreen is mixed with alcohol. Is very effectual against intermittent fever. This can also be used to treat sexually trans mitted disease as gonorrhea & in gonorrheal & other rheumatism. Wintergreen oil can be used for trigeminal neuralgia, & in subcutaneous & chronic cystitis.This oil is used as liniments & ointments for reliving pains in above mentioned cases.

4.

Aspirin is  a group of drugs called Salicylates. It is also known to treat mild to moderate pain, & to reduce fever or inflammation. It is sometimes used to treat or prevent heart attacks, strokes, & angina. On the other hand, the oil of wintergreen or methyl salicylate & also came from the same active ingredient, Salicylic acid. Commercially, it is used as a flavoring for candies & chewing gum & in the treatment of muscular aches & pains. When synthesized & sold as the oil of wintergreen itself, it can be sold as beverage.The 2 compounds indicated are both organic esters. An ester is a compound that is formed when an acid (containing the COOH group) reacts with an alcohol (containing an -OHgroup). In this experiment the experimenters will prepare two esters of o-hydroxy benzoic acid, more commonly known as salicylic acid. One of the esters, acetyl salicylic acid, is aspirin, common analgesic. They will synthesize aspirin by mixing salicylic acid with acetic anhydride. The second ester product is oil of wintergreen, or methyl salicylate, which we prepare by allowing salicylic acid to react with methyl alcohol. This compound, which has a familiar odor, is used as a flavoring agent in rubbing ointments.

Salicylic acid and acetic anhydride reacts to form acetylsalicylic acid and acetic acid.

Salicylic acid and methanol reacts to form methylsalicylate.