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Chapter 18: Q65E (page 594)

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

o-Hydroxyphenylacetaldehyde

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01

o-Hydroxyphenylaldehyde

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

02

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.

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Most popular questions from this chapter

The alkoxymercuration of alkenes involves the formation of an organomercury intermediate (I), which is reduced with NaBH4 to give an etherproduct. For each reaction below, predict the ether product and provide the mechanism formation.

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