Synthesis of 3-chlorobenzaldehyde

Preparation of 3-chlorobenzaldehyde

Preparation of 3-chlorobenzaldehyde

Preparation of 3-chlorobenzaldehyde

2 moles of tin(II) chloride dihydrate are dissolved in 600ml of concentrated hydrochloric acid in a 3-liter beaker. The solution is cooled to 5° C and 0.66 mole of m-nitrobenzaldehyde is added all at once with vigorous stirring and cooling in ice (temperature rise to about 100° C !!!). The resulting red solution of m-aminobenzaldehyde is cooled in ice-salt to 2° C and to the resulting slurry is dropped in a solution of sodium nitrite during 90 min, with vigorous stirring (temperature 0-5°C), through a dropping funnel whose tip dips into the reaction mixture; addition is stopped when the solution gives a positive starch-iodide reaction for free nitrous acid (about 5 ml remain out of a solution of 0.67 mole of sodium nitrite in 150 ml of water). The diazonium chloride solution is added with shaking to a copper(I) chloride solution at 75° C; the mixture is then treated with 840 ml of concentrated hydrochloric acid, set aside overnight and worked up by distillation in steam. m-Chlorobenzaldehyde, which passes over with the first 1.5 liter of distillate, is extracted several times several times in ether (2 x 150ml), being obtained in 75-79% yield with b.p. 84-86°/8 mm, 107-109°/26 mm.

J. S. Buck, W. S. Ide, Org. Syn., Coll. Vol. II, 130 (1943).

IUPAC Name

3-chlorobenzaldehyde

InChI

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

InChI Key

SRWILAKSARHZPR-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC(=C1)Cl)C=O

Depositor-Supplied Synonyms

3-CHLOROBENZALDEHYDE, 587-04-2, m-Chlorobenzaldehyde, Benzaldehyde, 3-chloro-, mcad, meta-Chlorobenzaldehyde, Benzaldehyde, m-chloro-, 3-chloro benzaldehyde, 3-chloro-benzaldehyde, SRWILAKSARHZPR-UHFFFAOYSA-N, SBB040204, NSC60107, 3-chloroben-zaldehyde, 5-Chloro-benzaldehyde, PubChem10800, AC1L1XFV, ACMC-1AJO5, AC1Q3K4E, SCHEMBL40399, C23403_ALDRICH, KSC270E8N, CCRIS 8613, DTXSID1074591, Benzaldehyde, m-chloro- (8CI), CTK1H0286, TIMTEC-BB SBB040204, Benzaldehyde, 3-chloro- (9CI), ZINC164556, STR00144, AKOS BBS-00003158, EINECS 209-596-9, ANW-33021, KM0229, MFCD00003350, NSC 60107, NSC-60107, ZINC00164556, AKOS000119909, AM81267, AS02776, MCULE-1383980732, RP20641, TRA0013503, ZF10006, AJ-16210, AK-68812, AN-46143, BC227688, BR-68812, CJ-02170, KB-31222, OR011042, ZB008200, AI3-10532, DB-024151, ST2410647, TL8003756, TR-020389, FT-0615453, ST50213346, A25258, Benzaldehyde, m-chloro-;meta-Chlorobenzaldehyde, 40381-EP2272517A1, 40381-EP2280000A1, 40381-EP2287141A1, 40381-EP2305679A1, 40381-EP2311830A1, I01-2835, F2190-0597, InChI=1/C7H5ClO/c8-7-3-1-2-6(4-7)5-9/h1-5

Removed Synonyms

C7H5ClO, MolPort-000-145-975, CID11477, c0124, RTR-020389

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