Synthesis of 4-nitrophenoxyacetic acid

Preparation of 4-nitrophenoxyacetic acid

The round bottom flask is charged with 35 g of para nitrophenol, 40 g of 50% sodium hydroxide solution, 24 g of chloroacetic acid and 200 ml of water. The reaction mixture is refluxed and at the end of the reaction the solution is no longer alkaline. Additionally 20 g of 50% sodium hydroxide solution, 12 g of chloroacetic acid and 50 ml of water are added, and the solution is boiled further until neutral pH. The reaction mixture is then acidified with hydrochloric acid and cooled, precipitated crude (4-nitrophenoxy)acetic acid is purified either by recrystallization from alcohol, or by dissolving 4-nitrophenoxyacetic acid in dilute sodium hydroxide solution and reprecipitating with hydrochloric acid. The yield of 4-nitrophenoxyacetic acid is 25-30 g as glistening platelets which melt at 183° C.

An advanced laboratory manual of organic chemistry, M. Heidelberger, 33-34, 1923

InChI

InChI=1S/C8H7NO5/c10-8(11)5-14-7-3-1-6(2-4-7)9(12)13/h1-4H,5H2,(H,10,11)

InChI Key

AVDLFIONKHGQAP-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC=C1[N+](=O)[O-])OCC(=O)O

MeSH Synonyms

(4-nitrophenoxy)acetic acid

Depositor-Supplied Synonyms

4-Nitrophenoxyacetic acid, 2-(4-Nitrophenoxy)acetic acid, 1798-11-4, (4-Nitrophenoxy)acetic acid, p-Nitrophenoxyacetic acid, Acetic acid, (4-nitrophenoxy)-, Acetic acid, 2-(4-nitrophenoxy)-, (4-Nitro-phenoxy)-acetic acid, Ba 2690, ACETIC ACID, p-NITROPHENOXY-, AVDLFIONKHGQAP-UHFFFAOYSA-N, EINECS 217-283-3, NSC 166278, BRN 2051970, AI3-52610, ACMC-209efx, 4-nitrophenoxy acetic acid, AC1L26HF, Oprea1_291146, (4-nitrophenoxy) acetic acid, (4-nitrophenoxy)-acetic acid, SCHEMBL656493, (4-Nitro phenoxy)acetic Acid, (4-Nitro phenoxy) acetic acid, AC1Q765M, ARONIS023189, CHEMBL177045, Jsp003701, Acetic acid, (p-nitrophenoxy)-, CTK3J3514, MolPort-000-886-171, 2-(4-nitro-phenoxy)-acetic acid, ALBB-000229, ANW-22987, BBL023111, NSC166278, SBB000363, STK093391, AKOS000264482, MCULE-4354028178, NSC-166278, RTR-049559, VZ29556, AJ-10426, AK116836, AM100400, AN-49909, I558, KB-40114, KB-88859, LS-12604, ST012638, ST2403979, TR-049559, 4CH-018689, FT-0689255, N0226, A-8201, 4-06-00-01302 (Beilstein Handbook Reference), AF-615/00098055, T5895623, I14-45124, 3B3-033612

Removed Synonyms

CID15720, T4666

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