Phenoxyacetic acid

Chemical properties

Phenoxyacetic acid has a sour, sweet odor and a honey-like taste.

Occurrence

Reported found in cocoa beans

The Uses of Phenoxyacetic acid

Phenoxyacetic acid is a flavoring ingredient.?Its photodegradation using titanium dioxide as photocatalyst has been studied. Selective separation of penicillin V from phenoxyacetic acid using liquid membranes consisting of 1,2-dichloroethane and Amberlite LA-2 as carrier has been studied.

The Uses of Phenoxyacetic acid

Fungicide; keratin exfoliative (to relieve and to soften calluses, corns, and other hard skin surfaces; applied as plasters, pads or in liquids).

Definition

ChEBI: Phenoxyacetic acid is a monocarboxylic acid that is the O-phenyl derivative of glycolic acid. A metabolite of 2-phenoxyethanol, it is used in the manufacture of pharmaceuticals, pesticides, fungicides and dyes. It has a role as a human xenobiotic metabolite, an Aspergillus metabolite, a plant growth retardant and an allergen. It is a monocarboxylic acid and an aromatic ether. It is functionally related to a glycolic acid. It is a conjugate acid of a phenoxyacetate.

Synthesis Reference(s)

Synthetic Communications, 16, p. 479, 1986 DOI: 10.1080/00397918608057726

General Description

Light tan powder or white solid.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

Phenoxyacetic acid reacts exothermically with all bases, both organic (for example, the amines) and inorganic.

Health Hazard

ACUTE/CHRONIC HAZARDS: Phenoxyacetic acid is a mild skin irritant.

Fire Hazard

Flash point data for Phenoxyacetic acid are not available; however Phenoxyacetic acid is probably combustible.

Synthesis

A Schlenk tube was charged with aryl iodides (1) (1.0 mmol), glycolic acid (228 mg, 3.0 mmol), CuI (19.0 mg, 0.1 mmol), Cs2CO3 (1.95 g, 6.0 mmol), and DMSO/H2O (2 mL/1 mL). The mixture was stirred for 24 h at 120 ℃ under Ar. The reaction mixture was allowed to cool to room temperature, poured into 5 mL of water, and then acidified to pH = 1 with 2 N HCl solution. The aqueous phase was extracted twice with EtOAc, and the combined organic layer was washed with H2O and brine, dried over anhydrous MgSO4, and concentrated under vacuum. Purification of the crude product by column chromatography (dichloromethane/methanol) afforded the desired product Phenoxyacetic acid, white solid, yield 133 mg, 88%. 

Purification Methods

Crystallise the acid from water or aqueous EtOH. [Beilstein 6 IV 634.]