Methyl iodide → Methyl 2-methyl-6-nitrobenzoate

HRID 2251833Notes

Reaction equation

HRID 2251833 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([OH:6])=[O:5].[C:14]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 160976-Methyl-2-nitrobenzoic acid

Product 1

HCID 596057Methyl 2-methyl-6-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-methyl-6-nitro-benzoic acid (5.6 g, 30.9 mmol, 1.0 eq, Aldrich) and acetone (100 mL) was added crushed K2CO3 (21.4 g, 154.6 mmol, 5 eq) and MeI (9.6 mL, 154.6 mmol, 5.0 eq). The reaction was heated to reflux for 15 h then cooled to RT, filtered and concentrated in vacuo. The filtrate was dissolved in EtOAc, washed with H2O and brine, dried (MgSO4) and concentrated in vacuo to give the desired compound as a reddish-brown oil which upon standing at RT crystallized to tan needles

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 15 h
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe filtrate was dissolved in EtOAc
  6. washwashed with H2O and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f3539eb52ee743f19a19cd5796610adb
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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