Synthesis of p-Phenetidine

Preparation of p-phenetidine

Preparation of p-phenetidine

Preparation of p-phenetidine

100 g. of p-nitrophenetole, 200 ml water and 10 ml conc. hydrochloric acid are placed in a flask or a sulfonating pot fitted with a good mechanical agitator. The temperature is raised to 60 °C, and iron filings (100 g.) are gradually introduced over 3-4 hours. When all the iron has been added the temperature is raised to 90 °C, where it is maintained until the reduction is complete. The supernatant aqueous liquor is poured or siphoned off, and the sludge is steam distilled with superheated steam at 160°-180 °C, when the p-phenetidine passes over, and is separated from the aqueous distillate by extraction with ether, and purified by distillation. p-Phenetidine is a liquid, b.p. 244 °C.

Systematic organic chemistry, by W. M. Cumming, 361, 1937.





InChI Key


Canonical SMILES


MeSH Synonyms

Aminophenetole, Ethoxyaniline, Phenetidine

Depositor-Supplied Synonyms

4-ETHOXYANILINE, p-Phenetidine, Phenetidine, 156-43-4, 4-Aminophenetole, p-Ethoxyaniline, p-Phenetidin, Benzenamine, 4-ethoxy-, p-Aminophenetole, 4-Ethoxybenzenamine, Phenethidine, 1-Amino-4-ethoxybenzene, 4-Phenetidine, 4-Aminoethoxybenzene, Aniline, p-ethoxy-, 4-ETHOXY-ANILINE, Ethyl p-aminophenol, p-Aminofenetol, p-Fenetidin, 4-Ethoxybenzeneamine, p-Fenetidin [Czech], p-Aminofenetol [Czech], NSC 3116, p-aminophenyl ethyl ether, UNII-9TSL224ZSE, CCRIS 2878, CHEBI:85505, IMPPGHMHELILKG-UHFFFAOYSA-N, 4-ethoxyphenylamine, EINECS 205-855-5, MFCD00007865, SBB040442, CP 5685, BRN 0606666, AI3-09042, DSSTox_CID_5864, DSSTox_RID_77954, DSSTox_GSID_25864, CAS-156-43-4, phenetylamine, 4-ethoxyanilin, 4-ethoxyyaniline, 4′-aminophenetol, p-aminoethoxybenzene, 4-ethoxy-phenylamine, PubChem9511, Para-aminoethoxybenzene, (4-ethoxyphenyl)-amine, 4-aminophenyl ethyl ether, ACMC-1BO2R, AC1L1S9J, AC1Q37IV, WLN: ZR DO2, 9TSL224ZSE, akos bbs-00003550, SCHEMBL15703, P14815_ALDRICH, KSC176I0N, MLS002454444, UN 2311 (Salt/Mix), BIDD:GT0388, AC1Q385A, CHEMBL250969, DTXSID0025864, CTK0H6406, NSC3116, HMS3041D03, ZINC391847, NSC-3116, Tox21_201946, Tox21_303334, ANW-21616, AR-1L1671, LS-894, STK397546, ZINC00391847, AKOS000100572, CS11879, MCULE-5015601132, NE10524, RP20364, TRA-0201284, NCGC00091785-01, NCGC00091785-02, NCGC00257138-01, NCGC00259495-01, AJ-21138, AK-96013, AN-23335, CJ-03523, KB-79914, OR034322, OR155931, SMR001252219, ZB012077, KB-204415, TR-033065, BB 0241911, P0090, ST24029073, ST45026313, AZ0001-0114, 4-13-00-01017 (Beilstein Handbook Reference), I01-0491, Q-200467, T5726400, F2190-0444, InChI=1/C8H11NO/c1-2-10-8-5-3-7(9)4-6-8/h3-6H,2,9H2,1H

Removed Synonyms

Aminophenetole, ETHOXYANILINE, 4-Dimethylaminopyridine, C8H11NO, CID9076, MolPort-000-871-470, RTR-033065, D010628, 15893-96-6, 659-34-7

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