Dimethylformamide → Chloro-N,N-dimethylformiminium chloride

HRID 2291069Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([CH:10]=[CH:11][C:12]([CH3:15])(O)[CH3:13])=[C:5]([CH3:16])[C:4]=1[CH3:17].P(Cl)(Cl)([Cl:20])=O.[C:23]([O-])(=[O:25])C.[Na+].[CH3:28][N:29]([CH3:32])[CH:30]=O>O>[CH3:28][N+:29]([CH3:32])=[CH:30][Cl:20].[Cl-:20].[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:23]=[O:25])=[C:5]([CH3:16])[C:4]=1[CH3:17]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 4-(4-methoxy-2,3,6-trimethylphenyl)-2-methyl-3-buten-2-ol (3.98 g, 0.017 mol) in 8 mL of N,N-dimethylformamide (DMF) was stirred in an ice bath and the Vilsmeier reagent, which was prepared from 2.1 mL (3.4 g, 0.022 mol) of phosphoryl chloride and 3.5 mL of DMF at about 10° C., was added dropwise. The temperature of the reaction mixture was allowed to rise to 80° C. within 1 hr. The mixture was stirred for 3 hrs at 80° C. and, with cooling (ice bath), a solution of sodium acetate (10g) in 25 mL of water was added dropwise. The resulting mixture was heated to 80° C. for 10 min. After cooling to room temperature, the product was extracted into ethyl ether. Removal of solvent in vacuo afforded an orange-colored substance. Crystallization from ethyl acetate-ethyl ether gave 2.2 g of the title compound as yellow crystals: mp 62°-64° C.

Workup

additionwas added dropwise
temperaturewith cooling (ice bath)
temperatureThe resulting mixture was heated to 80° C. for 10 min
temperatureAfter cooling to room temperature
extractionthe product was extracted into ethyl ether
customRemoval of solvent in vacuo
customafforded an orange-colored substance
customCrystallization from ethyl acetate-ethyl ether

Sources & evidence

ORD record: ord-615fac62f2fe4c6b86de3ab53a012dbc
Source dataset: uspto-grants-1986_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04619945

Reaction notes

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