Aspirin is acetylsalicylic acid (o-acetoxybenzoic acid, \(\left.0-\mathrm{CH}_{3} \mathrm{COO}-\mathrm{C}_{6} \mathrm{H}_{4} \mathrm{COOH}\right)\); oil of wintergreen is the ester, methyl salicylate. Outline the synthesis of these two compounds from phenol.

Short Answer

Expert verified
To synthesize acetylsalicylic acid (aspirin) and methyl salicylate (oil of wintergreen) from phenol, follow these steps: 1. Convert phenol to salicylic acid via the Kolbe-Schmitt reaction with NaOH and CO2, followed by acidification with HCl. 2. Synthesize aspirin by reacting salicylic acid with acetic anhydride in the presence of a strong acid catalyst. $$\text{C}_{6}\text{H}_{4}(\text{OH})\text{COOH} + (\text{CH}_{3}\text{CO})_{2}\text{O} \rightarrow \text{CH}_{3}\text{COOC}_{6}\text{H}_{4}\text{COOH} + \text{CH}_{3}\text{COOH}$$ 3. Synthesize oil of wintergreen by reacting salicylic acid with methanol in the presence of a strong acid catalyst. $$\text{C}_{6}\text{H}_{4}(\text{OH})\text{COOH} + \text{CH}_{3}\text{OH} \rightarrow \text{CH}_{3}\text{OC}_{6}\text{H}_{4}\text{COOH} + \text{H}_{2}\text{O}$$

Step by step solution

01

Convert phenol to salicylic acid

First, we need to convert phenol into salicylic acid. This can be done by the Kolbe-Schmitt reaction, in which phenol reacts with sodium hydroxide (NaOH) and carbon dioxide (CO2) to form sodium salicylate, followed by acidification to give salicylic acid. Reactions: 1. Phenol + NaOH -> Sodium phenoxide (NaOC6H5) 2. Sodium phenoxide + CO2 -> Sodium salicylate (NaOC6H4COO-) 3. Sodium salicylate + HCl -> Salicylic acid (C6H4(OH)COOH) + NaCl
02

Synthesis of Acetylsalicylic Acid (Aspirin)

To synthesize aspirin, we need to convert the salicylic acid obtained in step 1 into its acetyl derivative, acetylsalicylic acid. This can be done via an esterification reaction with acetic anhydride in the presence of or using a strong acid catalyst like sulfuric acid. Reaction: Salicylic acid (C6H4(OH)COOH) + Acetic anhydride ((CH3CO)2O) -> Acetylsalicylic acid (Aspirin) (CH3COOC6H4COOH) + Acetic acid (CH3COOH)
03

Synthesis of Methyl Salicylate (Oil of Wintergreen)

To synthesize methyl salicylate, we need to convert the salicylic acid obtained in step 1 into its methyl ester. This can be done by an esterification reaction with methanol in the presence of a strong acid catalyst like sulfuric acid or hydrochloric acid. Reaction: Salicylic acid (C6H4(OH)COOH) + Methanol (CH3OH) -> Methyl salicylate (Oil of Wintergreen) ( CH3OC6H4COOH) + Water (H2O) These steps outline the synthesis of both acetylsalicylic acid (aspirin) and methyl salicylate (oil of wintergreen) from phenol.

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