Synthesis of 4-(4-phenoxyphenyl)butanoic acid

Preparation of 4-(4-phenoxyphenyl)butanoic acid

Alternative Names: 4-(p-phenoxyphenyl)butyric acid; 4-(4-Phenoxy-phenyl)-butyric acid;

Preparation of 4-(4-phenoxyphenyl)butyric acid

Preparation of 4-(4-phenoxyphenyl)butyric acid

A mixture of the 500 g of 4-oxo-4-(4-phenoxyphenyl)butanoic acid, 350 g of potassium hydroxide, and 2500 ml of 85 % hydrazine hydrate in tri- or di-ethylene glycol is heated under reflux for 1.5 hours. The water formed is then distilled off through a descending condenser until the temperature of the reaction mixture has risen to 195° C, whereafter the solution is heated for a further 4 hours. After cooling, the solution is diluted with 2500 ml of water and poured slowly into 6N hydrochloric acid. The weight of dried product amounts to 95% of the theoretical (451 g), and the melting point is 64-66° C. 4-(4-Phenoxyphenyl)butyric acid is recrystallized from ligroin-benzene yielding pure product (m.p. 71-72° C).

J. Amer. Chem. Soc, 68, 2487 (1946).

IUPAC Name

4-(4-phenoxyphenyl)butanoic acid

InChI

InChI=1S/C16H16O3/c17-16(18)8-4-5-13-9-11-15(12-10-13)19-14-6-2-1-3-7-14/h1-3,6-7,9-12H,4-5,8H2,(H,17,18)

InChI Key

YTPRFJSWHCNPHB-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)OC2=CC=C(C=C2)CCCC(=O)O

Depositor-Supplied Synonyms

4-(4-phenoxyphenyl)butanoic acid, CHEMBL321615, 6958-94-7, 4-(4-Phenoxy-phenyl)-butyric acid, NSC66450, AC1L6NBH, AC1Q5W1C, CTK5D0540, MolPort-005-181-620, ALBB-013729, AR-1F6410, BDBM50060969, NSC-66450, AKOS005173995, MCULE-7383941639, KB-238506, Y-9988

Removed Synonyms

CID248891, 87689-56-3

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