4-Chloro-3-methylphenol → 1-Chloro-4-methoxy-2-methylbenzene

HRID 1163968Notes

Reaction equation

HRID 1163968 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[C:10](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:10])=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 17324-Chloro-3-methylphenolHCID 6328Methyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 4581561-Chloro-4-methoxy-2-methylbenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Chloro-3-methylphenol (28.5 g., 0.2 mole) was dissolved in 400 ml. of acetone. Potassium carbonate (33.1 g., 0.24 mole) and then methyl iodide (34.1 g., 0.24 mole) were added and the mixture stirred for 16 hours at room temperature. The reaction mixture was filtered and the filtrate evaporated to an oil containing solids. This residue was distributed between methylene chloride and water. The organic layer was separated, washed in sequence with two portions of 1 N sodium hydroxide, two portions of water and one portion of brine, dried over anhydrous magnesium sulfate and concentrated to yield 4-chloro-3-methylanisole as an oil [24.6 g., 86%, pnmr/CDCl3 /delta 2.3 (s, 3H), 3.7 (s, 3H) 6.9 (m, 3H)].

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated to an oil
  3. additioncontaining solids
  4. customThe organic layer was separated
  5. washwashed in sequence with two portions of 1 N sodium hydroxide, two portions of water and one portion of brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-43fac1609c3643f08c36493c1feaa599
Source dataset
uspto-grants-1983_01
Patent number
US04367234

Reaction notes

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