Phosphorus oxychloride → Benzaldehyde, 2,6-dichloro-4-(dimethylamino)-

HRID 746035Notes

Reaction equation

P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[N:10]([CH3:12])[CH3:11].[C:17]([O-])(=[O:19])C.[Na+]>CN(C)C=O>[Cl:6][C:7]1[CH:8]=[C:9]([N:10]([CH3:12])[CH3:11])[CH:13]=[C:14]([Cl:16])[C:15]=1[CH:17]=[O:19]

Participants

Conditions

Temperature: 100 °C

Procedure

Phosphoryl chloride (0.56 cm3, 6.1 mmol) was added dropwise to cooled N,N-dimethyl formamide (4 cm3) under nitrogen. 3,5-dichloro-N,N-dimethylaniline (1.16 g, 6.1 mmol) was then added to the solution which was then heated under nitrogen at 100° C. for 3 h. The solution was cooled, poured onto ice (6 g) and the mixture adjusted to pH 6 by addition of a saturated solution of sodium acetate. The suspended solid was collected and recrystallised from ethyl acetate-petroleum spirit 60°-80° C. mixture giving pale yellow needles of 2,6-dichloro-4-dimethylaminobenzaldehyde (0.8 g) mp 169°-71° C.

Workup

temperatureThe solution was cooled
additionpoured onto ice (6 g)
customThe suspended solid was collected
customrecrystallised from ethyl acetate-petroleum spirit 60°-80° C. mixture

Sources & evidence

ORD record: ord-b8681c6a7d1e4c479bb60b8b5c3977be
Source dataset: uspto-grants-1986_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04602041

Reaction notes

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