Synthesis of terephthalaldehyde

Preparation of terephthalaldehyde

Preparation of terephthalaldehyde

Preparation of terephthalaldehyde

The 1,4-bis(dichloromethyl)benzene (or 1,4-bis(dibromomethyl)benzene) 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 90-110°C. 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 terephthalaldehyde 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 recrystallized from water/methanol (90:10). The yield of terephthalaldehyde is 80%, m.p. 115 °C; b.p. 245-248 °C.

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

IUPAC Name

terephthalaldehyde

InChI

InChI=1S/C8H6O2/c9-5-7-1-2-8(6-10)4-3-7/h1-6H

InChI Key

KUCOHFSKRZZVRO-UHFFFAOYSA-N

Canonical SMILES

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

Depositor-Supplied Synonyms

TEREPHTHALALDEHYDE, 623-27-8, 1,4-Benzenedicarboxaldehyde, p-Phthalaldehyde, Terephthaldehyde, Terephthaladehyde, Terephthaldialdehyde, Terephthaldicarboxaldehyde, p-Formylbenzaldehyde, 4-Formylbenzaldehyde, Terephthalic aldehyde, Terephtaldehyde, 1,4-Diformylbenzene, p-Benzenedicarboxaldehyde, 1,4-Phthalaldehyde, Terephtaldehydes, Benzene-1,4-dicarboxaldehyde, 1,4-Benzenedialdehyde, Terephtaldehydes [French], NSC 13395, UNII-M2Y6E4N2TS, benzene-1,4-dicarbaldehyde, KUCOHFSKRZZVRO-UHFFFAOYSA-N, EINECS 210-784-8, MFCD00006949, ST067119, terephthalaldehyd, p-Phthaldialdehyde, p-Benzenedialdehyde, Terephthaladehyde (8CI), WLN: VHR DVH, 1,4-Benzenedicarbaldehyde, Terephtaldehydes [French], AC1L1Z0C, T2207_ALDRICH, M2Y6E4N2TS, SCHEMBL31171, KSC492I3L, ACMC-209n29, T2207_SIAL, 86410_FLUKA, CTK3J2435, MolPort-000-872-253, NSC13395, STR02396, ZINC1729595, 1,4-DICARBOXALDEHYDE-BENZENE, ANW-34159, CP0026, NSC-13395, SBB012343, ZINC01729595, AKOS000120450, CS11974, MCULE-5261864819, RP20105, RTR-021428, UPCMLD0ENAT5955267:001, AC-10411, AJ-31186, AK-40107, AN-46763, BP-12578, CJ-06929, CJ-29392, KB-64575, OR019902, DB-054132, LS-148713, ST2413817, TL8004110, TR-021428, FT-0606766, M-5853, A833718, I01-0590, T5955267, W-105009, 3B3-029979, InChI=1/C8H6O2/c9-5-7-1-2-8(6-10)4-3-7/h1-6

Removed Synonyms

CID12173, T0010

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