Methyl iodide → 876389-28-5

HRID 564285Notes

Reaction equation

HRID 564285 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[C:3]=1[CH3:11].[C:12](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:12])=[C:4]([CH3:10])[C:3]=1[CH3:11]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 108225484-bromo-2,3,6-trimethyl-phenol

Product 1

HCID 11557666876389-28-5

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2,3,6-trimethyl phenol (66.2 g; 0.294 mol) in acetone (2 L) was added potassium carbonate (203 g; 1.47 mol) at ambient temperature. Then MeI (91.4 ml; 1.47 mol) was added dropwise over 30 mins. Reaction was stirred overnight at ambient temperature. After this time the mixture was filtered, washing with acetone (2×200 ml) and the filtrate evaporated to give a red solid. The solid was taken up in DCM (1.2 L) and washed with 1M sodium thiosulfate (2×400 ml), half sat. brine (800 ml), dried (anh. MgSO4), filtered and the solvent evaporated to give a red oil (53.8 g; 80%). 1H NMR (300 MHz, CDCl3), δ/ppm; 2.23 (3H, s, Ar—CH3), 2.25 (3H, s, Ar—CH3), 2.32 (3H, s, Ar—CH3), 3.66 (3H, s, Ar—OCH3), 7.23 (1H, s, Ar—H).

Workup

  1. customReaction
  2. filtrationAfter this time the mixture was filtered
  3. washwashing with acetone (2×200 ml)
  4. customthe filtrate evaporated
  5. customto give a red solid
  6. washwashed with 1M sodium thiosulfate (2×400 ml), half sat. brine (800 ml)
  7. dry with materialdried (anh. MgSO4)
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. customto give a red oil (53.8 g; 80%)

Sources & evidence

ORD record
ord-319d5c8d34f24d5fbb732d8702b03016
Source dataset
uspto-grants-2011_11
Patent number
US08067642B2

Reaction notes

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