Water → HCID 22058675, compound

HRID 1828797Notes

Reaction equation

HRID 1828797 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:21][CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)(=O)=O.O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH2:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 148533-Chloro-4-methylphenolHCID 15712513HCID 15712513, compound

Product 1

HCID 22058675HCID 22058675, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-chloro-4-methylphenol (1.00 g) in N,N-dimethylformamide (8 ml) was added potassium carbonate powder (1.44 g) and the mixture was heated to 80° C. Thereto was added cyclopentylmethyl methanesulfonate (1.57 g) and the mixture was stirred at 120° C. for 3 hr. The reaction mixture was cooled to room temperature. Water was added and the mixture was extracted 3 times with hexane. The organic layers were combined and washed successively with 1N aqueous sodium hydroxide solution, water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by column chromatography (silica gel, hexane) to give 2-chloro-4-((cyclopentyl)methyloxy)toluene (1.46 g) as a colorless oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted 3 times with hexane
  3. washwashed successively with 1N aqueous sodium hydroxide solution, water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by column chromatography (silica gel, hexane)

Sources & evidence

ORD record
ord-a13f6feb2a0c48dfa2f0133a4dd0762b
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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