2-Phenylbutyric Acid → 2-(4-Chloromethylphenyl)-butyric acid

HRID 1277680Notes

Reaction equation

HRID 1277680 reaction equation
ClC1C=CC(OC)=C(C=1)C(NC[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH2:22][CH3:23])[C:19]([OH:21])=[O:20])=[CH:14][CH:13]=1)=O.C1(C(CC)C(O)=O)C=CC=CC=1.C=O.[ClH:41]>>[Cl:41][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH2:22][CH3:23])[C:19]([OH:21])=[O:20])=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 70122-Phenylbutyric AcidHCID 19933572Methanone hydrochlorideHCID 234531072-{4-[2-(5-Chloro-2-methoxybenzamido)-ethyl]-phenyl}-butyric acid

Product 1

HCID 204475132-(4-Chloromethylphenyl)-butyric acid

Procedure

The 2-[4-(2-aminoethyl)-phenyl]-butyric acid hydrochloride used as starting material is prepared in the following manner: 2-phenylbutyric acid is reacted with paraformaldehyde/hydrochloric acid to give 2-(4-chloromethylphenyl)-butyric acid (b.p. 173°-176° C./0.1 mm Hg). By the reaction thereof with potassium cyanide, there is obtained 2-(4-cyanomethylphenyl)-butyric acid (oil) which, after catalytic hydrogenation, gives 2-[4-(2-aminoethyl)-phenyl]-butyric acid hydrochloride; m.p. 128°-130° C.

Workup

  1. customis prepared in the following manner

Sources & evidence

ORD record
ord-f2b5760ef47046c1874f2c1f50f95b95
Source dataset
uspto-grants-1981_07
Patent number
US04278680

Reaction notes

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