Question

How would you prepare o-Hydroxyphenylacetaldehyde from phenol? More than one step is required.

o-Hydroxyphenylacetaldehyde

Short answer

The answer is

Step-by-step solution

o-Hydroxyphenylaldehyde

The o-Hydroxyphenylacetaldehyde is an aromatic compound containing alcohol and an aldehyde functional group. It can undergo nucleophilic substitution reactions.

Explanation

The reaction for the synthesis of o-Hydroxyphenylacetaldehyde from phenol is shown below.

The hydroxyl group in phenol is protected using beta-methoxy ethoxy methyl ether (MEM). It is then treated with an ethane dial to give the substituted product. The product obtained then undergoes a reaction with tosyl hydroxide (TsOH) and Lithium aluminum hydride (LAH) to give the reduced product. It is then treated with acid to remove the protection of the hydroxyl group.