DL-2-(4-chlorophenyl)propanoic acid → 2-(4-Chlorophenyl)-1-propanol

HRID 1440986Notes

Reaction equation

HRID 1440986 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9](O)=[O:10])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:12])[CH2:9][OH:10])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 102525DL-2-(4-chlorophenyl)propanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 5870302-(4-Chlorophenyl)-1-propanol

Procedure

The synthesis of intermediates leading to different values of m and X is within the capability of one skilled in the art. Example 3 details the method of making the compound wherein X is --CH(CH3)-- and m is 2. This synthesis starts with the reduction of 2-(4-chlorophenyl)propionic acid with lithium aluminum hydride, producing 2-(4-chlorophenyl)propanol. Oxidation of this alcohol with pyridinium chlorochromate in methylene chloride produces 2-(4-chlorophenyl)propionaldehyde. This aldehyde is then reacted with (carbethoxymethylene)triphenylphosphorane, yielding ethyl 4-(4-chlorophenyl)-2-pentenoate. Hydrogenation of this ester in the presence of platinum oxide produces ethyl 4-(4-chlorophenyl)pentanoate which is then hydrolyzed with sodium hydroxide to the corresponding pentanoic acid (II). The remaining steps of this synthesis are shown in Schema 1.

Workup

  1. customThe synthesis of intermediates

Sources & evidence

ORD record
ord-abff4d5dbdf543f1aa97eaa952bd0040
Source dataset
uspto-grants-1996_03
Patent number
US05502054

Reaction notes

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