Synthesis of p-tolualdehyde

Preparation of p-tolualdehyde

Alternative Names: P-Tolualdehyde; 4-METHYLBENZALDEHYDE; 4-Tolualdehyde; P-Formyltoluene; P-Tolylaldehyde;

Preparation of p-tolualdehyde

Preparation of p-tolualdehyde

To 30 g of freshly distilled toluene contained in a wide-necked vessel cooled with water, add, not too quickly, 45 g of pulverised, freshly prepared aluminium chloride and 5 g pure copper(I) chloride. The vessel is closed by a three-hole cork; in the middle hole is inserted a glass tube which carries a stirrer; the other holes are used for the inlet and outlet tubes. After the apparatus has been fastened firmly in a clamp it is immersed into a casserole filled with water at 20° C. A current, not too rapid, of carbon monoxide and hydrogen chloride gas is led in through the prong-shaped tube while the stirrer is set in motion. The carbon monoxide is passed first through a solution of 50% potassium hydroxide and then through a wash-bottle containing concentrated sulfuric acid. The hydrogen chloride is passed through a wash-bottle containing concentrated sulfuric acid. The gas currents are so regulated that the volume of the carbon monoxide is about twice as large as that of the hydrogen chloride. The escaping gas is led directly to the hood opening. In the course of an hour when about 1-2 litres of carbon monoxide have been passed into the mixture, the temperature rises to 25-30° C; the remainder of the gas is passed in during four to five hours. If the reaction mixture should become so viscous before the lapse of this time that the stirrer revolves only with difficulty, the reaction may be stopped. The viscid product is then poured into a large flask containing crushed ice; the p-tolualdehyde formed and any unattacked toluene is distilled over with steam. The distillate — oil and water — is then shaken up with a sodium bisulfite solution for a long time. The toluene, remaining undissolved, is separated in a dropping funnel. If the p-tolualdehyde-bisulphite compound should crystallise out, water is added until it dissolves. The filtered water solution is then treated with anhydrous sodium carbonate until it shows a decided alkaline reaction; the p-tolualdehyde is then again distilled over with steam. It is extracted from the distillate with ether. Upon evaporating the ether, from 20-22 g of perfectly pure p-tolualdehyde remains. Boiling-point, 204° C.

The practical methods of organic chemistry, by L. Gattermann, 303-304, 1909

IUPAC Name

4-methylbenzaldehyde

InChI

InChI=1S/C8H8O/c1-7-2-4-8(6-9)5-3-7/h2-6H,1H3

InChI Key

FXLOVSHXALFLKQ-UHFFFAOYSA-N

Canonical SMILES

CC1=CC=C(C=C1)C=O

MeSH Synonyms

4-methylbenzaldehyde, 4-tolualdehyde, p-tolualdehyde

Depositor-Supplied Synonyms

p-Tolualdehyde, 4-METHYLBENZALDEHYDE, 4-Tolualdehyde, p-Formyltoluene, p-Tolylaldehyde, 104-87-0, p-Toluylaldehyde, para-Tolualdehyde, p-Methylbenzaldehyde, Benzaldehyde, 4-methyl-, para-Methylbenzaldehyde, para-Toluyl aldehyde, Paratolualdehyde, 4-Methyl-Benzaldehyde, 4-Toluylaldehyde, PTAL, 4-Toluicaldehyde, NSC 2224, UNII-GAX22QZ28Q, CCRIS 2942, CHEMBL190927, CHEBI:28617, HSDB 5361, FXLOVSHXALFLKQ-UHFFFAOYSA-N, EINECS 203-246-9, AI3-24380, Tolualdehydes, p-tolu-aldehyde, 4-Formyltoluene, p-toluenealdehyde, p-toluic aldehyde, p-tolyl-methanone, p-Tolualdehyde, c, 4-methyl benzaldehyde, p-4-methylbenzaldehyde, PubChem15497, ACMC-1BNIE, AC1L1PER, AC1Q2LUR, TOLUALDEHYDE, P-, bmse000527, DSSTox_CID_21520, GAX22QZ28Q, DSSTox_GSID_41520, SCHEMBL29171, T35602_ALDRICH, KSC211Q5P, W306800_ALDRICH, Jsp000473, 89850_FLUKA, TIMTEC-BB SBB040232, NSC2224, MolPort-000-141-279, ZINC896404, METHYL, (4-FORMYLPHENYL)-, NSC-2224, AKOS BBS-00003200, Tox21_304012, ANW-15131, BDBM50159265, LABOTEST-BB LT00930011, LABOTEST-BB LT03333783, ZINC00896404, AKOS000119345, AS02824, MCULE-2461351642, PS-5663, RP19375, RTR-001051, TRA0056352, NCGC00357225-01, AC-16956, AJ-24233, AK-65210, AN-24696, BC211019, CAS-104-87-0, CJ-04490, LS-25098, OR034328, OR196956, OR196957, OR243068, ZB015084, DB-003768, ST2418483, TR-001051, FT-0652962, LT00930011, T0259, C06758, A801081, 3B4-1127, I01-5966, W-108803, UNII-ALC105UA3K component FXLOVSHXALFLKQ-UHFFFAOYSA-N, InChI=1/C8H8O/c1-7-2-4-8(6-9)5-3-7/h2-6H,1H

Removed Synonyms

FEMA No. 3068, FEMA 3068, CID7725, c0201, T1073

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