Methyl iodide → Methyl o-toluate

HRID 2231349Notes

Reaction equation

HRID 2231349 reaction equation
[C:1]1([CH3:10])[C:2]([C:7]([OH:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.IC.[C:13](=O)(O)[O-].[Na+]>CN(C)C=O.O>[C:1]1([CH3:10])[C:2]([C:7]([O:9][CH3:13])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 83732-Methylbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 33094Methyl o-toluateYield 90.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of o-toluic acid (15 g, 0.11 mole), iodomethane (51 g, 0.36 mole) and anhydrous sodium bicarbonate (25.2 g, 0.3 mole) in dry dimethylformamide (60 ml) was stirred at 70° (oil bath temperature) under an atmosphere of nitrogen for 3.5 hours. The resulting mixture was diluted with water (200 ml) and extracted with ethyl ether (3×100 ml). The combined extracts were washed several times with water, dried over anhydrous MsGO4 and evaporated in vacuo to give the title ester compound (15 g, 90.6%) as an oil with a consistent H1 -NMR spectrum.

Workup

  1. extractionextracted with ethyl ether (3×100 ml)
  2. washThe combined extracts were washed several times with water
  3. customdried over anhydrous MsGO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-761c03efbc2e46a7b387dde135e8892c
Source dataset
uspto-grants-1988_11
Patent number
US04782085

Reaction notes

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