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Chapter 20: 61E (page 678)

Propose a synthesis of the anti-inflammatory drug Fenclorac from phenyl cyclohexane.

Short Answer

Expert verified

The Fenclorac synthesis from phenyl cyclohexane can be proposed.

Step by step solution

01

The alcohol gets converted into aldehyde

The benzene can be brominated for the yield of bromophenylcyclohexane. The Grignard reagent can be produced by converting bromide when it is treated with ether. Then it reacts with formaldehyde to form primary alcohol. The alcohol will be converted into aldehyde to oxidize Dess-Martin periodinane. A chlorine can be substituted into an aldehydic group as-CHO is meta-directing.

02

Process for the yield of Fenclorac

The aldehyde treatment with NaCN will yield a cyanohydrin when hydrolyzed with hydroxy acid. The hydroxyl group can be replaced using Cl when treated with SOCl2 for the Fenclorac yield.

03

Fenclorac synthesis from phenycyclohexane

The synthesis can be shown as,

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Most popular questions from this chapter

would you expect the following carboxylic acid to be more acidic or less acidic than benzoic acid? Explain (Reddish brown=Br)

How could you convert butanoic acid into the following compounds?
Write each step showing the reagents needed.
(a) 1-Butanol (b) 1-Bromobutane (c) Pentanoic acid
(d) 1-Butene (e) Octane

The following pKavalues have been measured. Explain why a hydroxyl group in the para position decreases the acidity while a hydroxy group in the meta position increases the acidity.

How could you convert each of the following compounds into butanoic acid? Write each step showing the reagents needed.

(a) 1-Butanol

(b) 1-Bromobutane

(c) 1-Butene

(d) 1-Bromopropane

(e) 4-Octene

Dicarboxylic acids have two dissociation constants, one for the initial dissociation into a monoanion and one for the second dissociation into a dianion. For oxalic acid, HO2C-CO2Hthe first ionization constant is pKa1=1.2and the second ionization constant is pKa2=4.2. Why is the second carboxyl group far less acidic than the first?
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