Phosphorus pentachloride → Phosphorus oxychloride

HRID 1284515Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5](O)=[O:6].[P:12]([Cl:17])(Cl)(Cl)([Cl:14])[Cl:13]>>[P:12]([Cl:17])([Cl:14])([Cl:13])=[O:6].[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]([Cl:13])=[O:6]

Participants

Reactant 2

HCID 24819Phosphorus pentachloride

HCID 136326323-Chloro-5-methylbenzoic acid

Product 2

HCID 24813Phosphorus oxychloride

HCID 150959783-Chloro-5-methylbenzoyl chloride

Procedure

A mixture of 3-chloro-5-methylbenzoic acid (9.4 g) and phosphorous pentachloride (11.6 g) is stirred at room temperature for 1 hour and then distilled to yield phosphorous oxychloride, b.p. 45°/85 mm and 3-chloro-5-methylbenzoyl chloride, b.p. 56°/0.1 mm (10 g).

Workup

distillationdistilled

Sources & evidence

ORD record: ord-b6d91ff516594d6e81c5e1657dc9806c
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04563465

Reaction notes

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