Methyl iodide → 1-Chloro-4-isopropyl-2-methoxybenzene

HRID 2266077Notes

Reaction equation

HRID 2266077 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][C:3]=1[OH:11].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=1[CH:20]([CH3:22])[CH3:21].[C:23]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:9])[CH3:10])=[CH:4][C:3]=1[O:11][CH3:13].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:23])=[CH:15][C:14]=1[CH:20]([CH3:22])[CH3:21]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 183278444-Chloro-3-isopropylphenolHCID 595964872-Chloro-5-isopropylphenol

Product 2

HCID 589280561-Chloro-4-isopropyl-2-methoxybenzeneHCID 589770251-Chloro-2-isopropyl-4-methoxy-benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-chloro-5-isopropyl-phenol and 4-chloro-3-isopropyl-phenol from step 1 (8.694 g, 47.1 mmol) in 50 mL DMF was added K2CO3. Iodomethane (3.5 mL, 56.5 mmol) was added and the mixture was warmed to 50° C. After 4 hours H2O was added. The mixture was extracted with ethyl acetate, washed with H2O, washed and washed with brine. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give 1-chloro-4-isopropyl-2-methoxy-benzene and 1-chloro-2-isopropyl-4-methoxy-benzene (9.289 g) as a 7:3 inseparable mixture in the form of a pale yellow oil, which was used directly in the following step.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with H2O
  3. washwashed
  4. washwashed with brine
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9af79a2969a141498e674530ae06e5d2
Source dataset
uspto-grants-2010_12
Patent number
US07858632B2

Reaction notes

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