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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

How would you prepare the following ethers using a Williamson synthesis?

  1. Methyl propyl ether
  2. Anisole (methyl phenyl ether)
  3. Benzyl isopropyl ether
  4. Ethyl 2,2-dimethylpropyl ether

How would you prepare the following ethers using a Williamson synthesis?

  1. Methyl propyl ether
  2. Anisole (methyl phenyl ether)
  3. Benzyl isopropyl ether
  4. Ethyl 2,2-dimethylpropyl ether

Name the following ethers:

d)

Anethole, , C10H12Oa major constituent of the oil of anise, has the NMR spectrum shown. On oxidation with Na2Cr2O7, anethole yields p-methoxybenzoic acid. What is the structure of anethole? Assign all peaks in the NMR spectrum, and account for the observed splitting patterns

Anethole, \({C_{10}}{H_{12}}O\), a major constituent of the oil of anise, has the \({}^1H\) NMR spectrum shown. On oxidation with \(N{a_2}C{r_2}{O_7}\), anethole yields p-methoxybenzoic acid. What is the structure of anethole? Assign all peaks in the NMR spectrum, and account for the observed splitting patterns.
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