2-Chlorobenzaldehyde → 2-Chlorobenzoyl chloride

HRID 2166670Notes

Reaction equation

HRID 2166670 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[Cl:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=[O:11].[Cl:16]Cl>>[Cl:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]([Cl:16])=[O:11]

Participants

4

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 24526ChlorineHCID 24819Phosphorus pentachloride

Product 1

HCID 691102-Chlorobenzoyl chloride

Conditions

Temperature
160 °C

Procedure

Phosphorus pentachloride (41.5 g, 0.2 mole) was added to 2-chlorobenzaldehyde (289.7 g, 2.0 mole, 97%). After the ensuing exotherm had subsided, the resulting red solution was heated to 160° C. A stream of chlorine was introduced through a sparge tube into the solution for a period of six hours. (Gas chromatography indicated 96.5% conversion.) The solution was then cooled and distilled under reduced pressure giving 325.4 grams of 2-chlorobenzoyl chloride which boiled at 135° to 140° C. at 16 millimeters of mercury. The yield of the desired product was 93% (98.5% pure).

Workup

  1. temperature(Gas chromatography indicated 96.5% conversion.) The solution was then cooled
  2. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-c7d17bb90e384aceac54122981dcce91
Source dataset
uspto-grants-1983_06
Patent number
US04388251

Reaction notes

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