Methyl iodide → Methyl 3-methoxy-2-methylbenzoate

HRID 1859816Notes

Reaction equation

HRID 1859816 reaction equation
[OH:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:13][Si]([N-][Si](C)(C)C)(C)C.[K+].CI>CN(C=O)C.C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:13][O:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 12488879Methyl 3-hydroxy-2-methylbenzoate

Product 1

HCID 12527049Methyl 3-methoxy-2-methylbenzoateYield 93.8%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 13.98 g (0.0841 mol) of methyl 3-hydroxy-2-methylbenzoate in 120 mL of DMF was cooled in ice and treated dropwise with 200 mL (0.1 mol) of a 0.5 M solution of KHMDS in toluene. After stirring for 10 minutes, 7.8 mL (0.126 mol) of methyl iodide was added and the solution allowed to stir at room temperature overnight. The solution was diluted with EtOAc and washed twice with 6% HCl, 3 times with H2O, 10% NaHSO3, then saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left 14.22 g (93.8% yield) of the product as a golden oil. The structure was confirmed by NMR and mass spectroscopy. MS m/z 181 (M+H+).

Workup

  1. stirringto stir at room temperature overnight
  2. washwashed twice with 6% HCl, 3 times with H2O, 10% NaHSO3
  3. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-2c877693cffa488f811be25d8675b025
Source dataset
uspto-grants-2003_03
Patent number
US06528535B2

Reaction notes

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