Synthesis of 4-nitrophenetole

Preparation of 4-nitrophenetole

Preparation of 4-nitrophenetole

Preparation of 4-nitrophenetole

To prepare the 4-nitrophenetole, 0.25 g gramequivalent of metallic sodium is dissolved in 300 ml of absolute ethanol to which the 4-nitrophenol, dissolved in a little absolute ethanol is then added. After the addition of the 0.2 mole of ethyl iodide (alternatively ethyl bromide),  the mixture is heated under reflux with stirring and exclusion of moisture for 5 hours. The alcohol is distilled off from the reaction mixture to a substantial extent through a 20-cm Vigreux column with stirring and the cooled distillation residue is poured into 100 ml of 5% caustic sodium carbonate; the organic phase is extracted several times with diethyl ether, washed with water, and dried with calcium chloride; the solvent is distilled off, and the residue is fractionated at 112-115 °C/3 mm or recrystallized from ethanol/water. Unchanged 4-nitrophenol can be recovered by acidifying the aqueous alkaline solution and extracting it with ether. The yield of 4-nitrophenetole is 60%, m.p. 60°C.

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 208-210, (1973)

IUPAC Name

1-ethoxy-4-nitrobenzene

InChI

InChI=1S/C8H9NO3/c1-2-12-8-5-3-7(4-6-8)9(10)11/h3-6H,2H2,1H3

InChI Key

NWPKEYHUZKMWKJ-UHFFFAOYSA-N

Canonical SMILES

CCOC1=CC=C(C=C1)[N+](=O)[O-]

MeSH Synonyms

1-ethyl-4-nitrophenyl ether, 4-nitrophenetol, p-nitrophenetol, p-nitrophenetole, para-nitrophenetol

Depositor-Supplied Synonyms

4-NITROPHENETOLE, 1-Ethoxy-4-nitrobenzene, p-Nitrophenetole, 100-29-8, Benzene, 1-ethoxy-4-nitro-, Phenetole, p-nitro-, p-Ethoxynitrobenzene, 4-Ethoxynitrobenzene, p-Nitrophenetol, Ethyl p-nitrophenyl ether, 4-Nitrophenetol, NSC 9812, p-Nitrophenetol [German], 1-ethoxy-4-nitro-benzene, CCRIS 2333, HSDB 5333, NWPKEYHUZKMWKJ-UHFFFAOYSA-N, EINECS 202-837-9, SBB058653, BRN 0972473, AI3-00233, ST50405193, PubChem3190, 4-ethoxy-1-nitrobenzene, ACMC-1BQZ9, DSSTox_CID_6655, UNII-O0A69I1MCU, WLN: WNR DO2, AC1L1OW1, Benzene,1-ethoxy-4-nitro-, DSSTox_RID_78176, O0A69I1MCU, DSSTox_GSID_26655, SCHEMBL45896, Phenetole, p-nitro- (8CI), CHEMBL3182742, CTK3J8741, NSC9812, MolPort-000-183-596, NSC-9812, ZINC1700199, Tox21_200729, 8076AF, ANW-14212, ZINC01700199, AKOS002685528, MCULE-1766475730, NCGC00248812-01, NCGC00258283-01, AJ-30458, AK135526, CAS-100-29-8, CJ-28691, LS-30334, OR019997, OR145690, KB-218814, TC-102957, N0216, 4-06-00-01283 (Beilstein Handbook Reference), A800088, I01-5242, 3B3-030121, InChI=1/C8H9NO3/c1-2-12-8-5-3-7(4-6-8)9(10)11/h3-6H,2H2,1H

Removed Synonyms

C8H9NO3, CID7495

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