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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

p-Aminobenzoic acid (PABA) is widely used as a sunscreen agent. Propose a synthesis of PABA starting from toluene.

Nitriles can be converted directly to esters by the Pinner reaction, which first produces an iminoester salt that is isolated and then treated with water to give the final product. Propose a mechanism for the Pinner reaction using curved arrows to show the flow of electrons at each step.

Calculate the percentages of dissociated and undissociated forms present in the following solutions:

(a) 0.0010Mglycolic acid (HOCH2CO2H;pKa=3.83) at pH=4.50

(b) 0.0020Mpropanoic acid (pKa=4.87 ) at pH=5.30

How would you carry out the following transformations?

Draw structures corresponding to the following IUPAC names:

(a) 2,3-Dimethylhexanoic acid

(b) 4-Methylpentanoic acid

(c)trans-1,2-Cyclobutanedicarboxylic acid

(d)o-Hydroxybenzoic acid

(e) (9Z,12Z)-9,12-Octadecadienoic acid

(f) 2-Pentenenitrile
See all solutions

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