Synthesis of 4-cyanobenzaldehyde

Preparation of 4-cyanobenzaldehyde

Alternative Names: 4-Formylbenzonitrile; p-Cyanobenzaldehyde; Benzonitrile, 4-formyl-; p-Formylbenzonitrile;

Preparation of 4-cyanobenzaldehyde (4-Formylbenzonitrile; p-Cyanobenzaldehyde; Benzonitrile, 4-formyl-; p-Formylbenzonitrile)

Preparation of 4-cyanobenzaldehyde (4-Formylbenzonitrile; p-Cyanobenzaldehyde; Benzonitrile, 4-formyl-; p-Formylbenzonitrile)

A mixture of 1 equiv. of terephthalaldehyde and 1.1 equiv. of hydroxylamine hydrochloride are mixed with the dimethylsulfoxide until the homogeneous mixture is obtained (3-5 volumes) and the obtained mixture is stirred at 90° C for 1-2 hours. The reaction is monitored by TLC (ethyl acetate:hexane 5:95) and when is completed the mixture is cooled and poured in water,  the reaction product is extracted with ether, dried and the ether is removed by evaporation affording 98% of the 4-cyanobenzaldehyde.

J. K. Augustine, et al. Synlett, 2223-2227, (2011) (supporting information)

IUPAC Name

4-formylbenzonitrile

InChI

InChI=1S/C8H5NO/c9-5-7-1-3-8(6-10)4-2-7/h1-4,6H

InChI Key

WZWIQYMTQZCSKI-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC=C1C=O)C#N

MeSH Synonyms

4-cyanobenzaldehyde

Depositor-Supplied Synonyms

4-Cyanobenzaldehyde, 4-Formylbenzonitrile, 105-07-7, p-Cyanobenzaldehyde, Benzonitrile, 4-formyl-, p-Formylbenzonitrile, Terephthalaldehydonitrile, Benzaldehyde, p-cyano-, Benzonitrile, p-formyl-, USAF KF-1, 4-FormYl-Benzonitrile, p-Cyanobenzenecarboxaldehyde, NSC 5091, CHEMBL1922276, WZWIQYMTQZCSKI-UHFFFAOYSA-N, EINECS 203-267-3, SBB008634, 4-formylbenzenecarbonitrile, p-cyano benzaldehyde, 4-cyano benzaldehyde, 4-cyano-benzaldehyde, 4-cyanobenzal-dehyde, 4-formyl benzonitrile, PubChem3118, PubChem8078, WLN: VHR DCN, ACMC-1BQT2, AC1L24HT, AC1Q6PT6, AC1Q6PT7, SCHEMBL7047, 4-methanoylbenzenecarbonitrile, C89609_ALDRICH, KSC176G9L, ARONIS24248, Jsp000488, Terephthalaldehydonitrile (8CI), 28350_FLUKA, CTK0H6395, NSC5091, MolPort-000-145-882, ACN-S002279, ACT01162, ALBB-005986, NSC-5091, STR00719, AC-283, ANW-15169, BBL022958, BDBM50358749, STK501695, ZINC00156750, AKOS000119506, AS02996, EBD3315213, FR-2351, MCULE-7602188115, PS-5292, RP19952, RTC-020900, TRA0100444, AJ-13880, AK-41243, AN-16007, BC209249, BP-11467, BR-41243, CJ-01543, KB-38381, LS-24982, SC-00211, ZB006437, AB1002960, DB-006791, TC-020900, TL8000196, AM20060796, BB 0260077, FT-0601275, ST24029062, ST50946585, EN300-20402, BENZALDEHYDE,4-CYANO MFC8 H5 N1 O1, C-4550, A801147, I01-0350, 3B3-002102, InChI=1/C8H5NO/c9-5-7-1-3-8(6-10)4-2-7/h1-4,6

Removed Synonyms

4-Chlorobenzaldehyde, CYANOBENZALDEHYDE(4-), TIMTEC-BB SBB008634, CID66042, c0443, 104-88-1

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