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

HRID 81751Notes

Reaction equation

HRID 81751 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-3b7131fca7064fffac7894f87ece74f2
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Reaction notes

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