Pyridine → Benzoyloxymethylpyridinium chloride

HRID 4721

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:7]([O:15][CH2:16][Cl:17])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[K+].[Br-]>>[Cl-:17].[C:7]([O:15][CH2:16][N+:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Reactant 3

HCID 1049Pyridine

HCID 79257Chloromethyl benzoate

HCID 253877Potassium Bromide

Product 1

HCID 12602695Benzoyloxymethylpyridinium chloride

Procedure

A mixture containing 0.79 g (0.01 mol) pyridine and 1.7 g (0.01 mol) chloromethyl benzoate was allowed to react at ambient temperature for 24 hr. Trituration in anhydrous ether followed by filtration under nitrogen gave 1.2 g (0.005 mol), 50%, 29, mp 197°-199° (dec); ir (KBr) 3440, 3020, 1710, 1610, 1475, 1265, 1150, 1085, 870 and 700 cm-1 ; pmr (D2O) δ 7.0-10.0 (m, 10H) and 6.6 (s, 2H) ppm.

Workup

customto react at ambient temperature for 24 hr
filtrationTrituration in anhydrous ether followed by filtration under nitrogen
customgave 1.2 g (0.005 mol), 50%, 29, mp 197°-199° (dec)

Sources & evidence

ORD record: ord-d6803dbfbc1e4f0fbfab242ee261a3d9
Source dataset: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04727151

Linked notes

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