Synthesis of 4-chlorobenzaldehyde

Preparation of 4-chlorobenzaldehyde

Preparation of 4-chlorobenzaldehyde

Preparation of 4-chlorobenzaldehyde

The 4-chlorobenzal chloride (or 4-chlorobenzal bromide) is stirred with eight times its weight of concentrated sulfuric acid in a three-necked flask with a ground sleeve, stirrer, reflux condenser, and a wide capillary serving as gas-inlet tube. Nitrogen is passed in through the capillary, and simultaneously the vacuum of a water pump is applied to the upper end of the reflux condenser. A vigorous evolution of hydrogen chloride (or hydrogen bromide) takes place at room temperature if not the reaction mixture is gently heated in the water bath (or oil bath). The reaction mixture changes the color to an intense red-brown color and the evolution of hydrogen chloride (or hydrogen bromide) ceases after about 1-2 hours. Then the mixture is poured on to ice and the 4-chlorobenzaldehyde formed is extracted several times with ether, the ethereal extracts are neutralized with sodium bicarbonate solution and then washed with water and dried over magnesium sulfate. After evaporation of the ether, the residue is distilled in vacuo or recrystallized from ligroin. The yield of 4-chlorobenzaldehyde is 70%, m.p. 48 °C; b.p. 213-214 °C; b.p.111/20mm°C.

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 203-204, (1973)

IUPAC Name

4-chlorobenzaldehyde

InChI

InChI=1S/C7H5ClO/c8-7-3-1-6(5-9)2-4-7/h1-5H

InChI Key

AVPYQKSLYISFPO-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC=C1C=O)Cl

MeSH Synonyms

4-chlorobenzaldehyde, p-chlorobenzaldehyde

Depositor-Supplied Synonyms

4-Chlorobenzaldehyde, 104-88-1, P-CHLOROBENZALDEHYDE, Benzaldehyde, 4-chloro-, Benzaldehyde, p-chloro-, 4-chloro-benzaldehyde, p-Chlorobenzenecarboxaldehyde, 4-Chlorobenzenaldehyde, PCAD, CCRIS 857, PARA-CHLOROBENZALDEHYDE, AVPYQKSLYISFPO-UHFFFAOYSA-N, NSC 2078, EINECS 203-247-4, MFCD00003379, SBB040227, AI3-52280, 4-Chlorbenzaldehyd, 4-Chlorobenzaldehyd, parachlorobenzaldehyde, p-chloro benzaldehyde, p-chloro-benzaldehyde, 4-chloro benzaldehyde, Benzaldehyde,p-chloro-, 4-chlorobenzoic aldehyde, AC1L1PEU, (4-chlorophenyl)methanone, DSSTox_CID_1860, ACMC-2098dr, bmse001029, AC1Q3JE4, AC1Q6Q6S, SCHEMBL1919, CHEMBL1474, DSSTox_RID_76369, DSSTox_GSID_21860, KSC178I3F, UNII-E67727UP9Z, 112216_ALDRICH, 23491_FLUKA, CTK0H8432, TIMTEC-BB SBB040227, NSC2078, MolPort-000-871-202, E67727UP9Z, ZINC896325, ACT07087, NSC-2078, STR00145, AKOS BBS-00003190, Tox21_200136, ANW-15133, AR-1G1768, BBL022959, LABOTEST-BB LT00928810, LABOTEST-BB LT03330752, LS-382, STK200392, ZINC00896325, AKOS000118927, AS02986, CS14843, LS10198, MCULE-4973481070, MP-2171, PS-9029, RP20640, RTR-001052, TRA0003207, NCGC00091804-01, NCGC00091804-02, NCGC00091804-03, NCGC00257690-01, AC-11571, AJ-24231, AK-76679, CAS-104-88-1, CJ-04489, KB-47504, OR034012, OR155772, OR196968, ZB015083, AB1002510, DB-023682, KB-204426, KB-241739, ST2411353, TR-001052, FT-0618168, ST50213377, C06648, 34650-EP2286811A1, 34650-EP2301536A1, 34650-EP2301538A1, 34650-EP2305679A1, 34650-EP2311455A1, 34650-EP2311814A1, 153316-EP2286811A1, 3B4-0173, I01-0456, W-108802, InChI=1/C7H5ClO/c8-7-3-1-6(5-9)2-4-7/h1-5

Removed Synonyms

null, p-Cyanobenzaldehyde, 4-Cyanobenzaldehyde, 4-Formylbenzonitrile, C7H5ClO, CYANOBENZALDEHYDE(4-), TIMTEC-BB SBB008634, CID7726, c0125, c0418, C052044, 105469-22-5

Share This

Leave a Reply

Your email address will not be published. Required fields are marked *