Guaiacol → 2-Chloro-4-(2-methoxyphenoxy)pyridine

HRID 910895Notes

Reaction equation

HRID 910895 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].[H-].[Na+].[Cl:12][C:13]1[CH:18]=[C:17]([N+]([O-])=O)[CH:16]=[CH:15][N:14]=1>>[Cl:12][C:13]1[CH:18]=[C:17]([O:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH:16]=[CH:15][N:14]=1

Participants

4

Reactant 3

HCID 460GuaiacolHCID 24758Sodium hydrideHCID 7351522-Chloro-4-nitropyridine

Product 1

HCID 637779562-Chloro-4-(2-methoxyphenoxy)pyridineYield 97%

Procedure

Using the method of Example 3, Step A, 2-methoxyphenol (2.35 g, 18.9 mmol), 60% sodium hydride in mineral oil (0.757 g, 18.9 mmol), and 2-chloro-4-nitropyridine (3.00 g, 18.9 mmol) were reacted to provide 2-chloro-4-(2-methoxyphenoxy)pyridine (4.32 g, 96.9% yield) as a white powder. 1H NMR (CDCl3) δ 8.20 (d, 1H), 7.27 (m, 1H), 7.10 (d, 1H), 6.99-7.06 (m, 2H), 6.72-6.75 (m, 2H), 3.79 (s, 3H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-cec637bcf8014dce89358aa98fefce7d
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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