Convert Phenol to oil of Winter green

Answer

To convert phenol to oil of wintergreen (methyl salicylate), we can follow a two-step synthetic pathway. Here’s a detailed step-by-step solution:

### Step 1: Convert Phenol to Salicylic Acid
1. **Starting Material**: Begin with phenol (C6H5OH).
2. **Reagent**: Treat phenol with carbon tetrachloride (CCl4) in the presence of sodium hydroxide (NaOH). This reaction is known as the Riemer-Tiemann reaction.
3. **Reaction**: The hydroxyl group (–OH) of phenol will be ortho- or para-hydroxylated to form salicylic acid (2-hydroxybenzoic acid).
4. **Product**: The product of this reaction is salicylic acid (C6H4(OH)(COOH)).

### Step 2: Convert Salicylic Acid to Methyl Salicylate
1. **Starting Material**: Use the salicylic acid obtained from the previous step.
2. **Reagent**: Treat salicylic acid with methanol (CH3OH) in the presence of sulfuric acid (H2SO4) as a catalyst.
3. **Reaction**: This reaction involves the esterification of salicylic acid with methanol, where the hydroxyl group of the carboxylic acid (–COOH) reacts with methanol to form an ester.
4. **Product**: The final product is methyl salicylate (C6H4(OH)(COOCH3)), which is also known as oil of wintergreen.

### Summary of the Reaction Sequence
1. **Phenol + CCl4 + NaOH → Salicylic Acid**
2. **Salicylic Acid + CH3OH + H2SO4 → Methyl Salicylate (Oil of Wintergreen)**

### Final Product
The final product, methyl salicylate, is characterized by its pleasant wintergreen aroma and is used in various applications, including as a flavoring agent and in topical analgesics.

---