Methyl iodide → HCID 13229641, compound

HRID 1730964Notes

Reaction equation

HRID 1730964 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:12]=[C:11]([CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15])[CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1.[CH3:21]I.[H-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:12]=[C:11]([C:13]([CH3:21])([CH3:18])[C:14]([O:16][CH3:17])=[O:15])[CH:10]=[CH:9][N:8]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21494426HCID 21494426, compound

Product 1

HCID 13229641HCID 13229641, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(2-p-chlorophenoxy-4-pyridyl)propionate (3.13 g) is treated with methyl iodide in the presence of 50 % sodium hydride in anhydrous tetrahydrofuran in a nitrogen atmosphere at room temperature for 1 hour and then at 40° C for 30 minutes, whereby methyl 2-(2-p-chlorophenoxy-4-pyridyl)isobutyrate (2.59 g) is obtained as crystals melting at 92° to 92.5° C. Then, this substance is treated with a mixture of 20 % aqueous potassium hydroxide and 95 % ethanol with refluxing for 10 minutes, whereby 2-(2-p-chlorophenoxy-4-pyridyl)isobutyric acid (2.35 g) is obtained as crystals melting at 135° to 136° C.

Sources & evidence

ORD record
ord-8cea2132c34c4acba7f26c0e1f760f18
Source dataset
uspto-grants-1976_11
Patent number
US03994908

Reaction notes

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