4-Chloro-3-methylphenol → HCID 18621211, compound

HRID 1861986Notes

Reaction equation

HRID 1861986 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19].CCOC(C)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:18]([CH3:17])(=[O:20])=[O:19])=[CH:4][C:3]=1[CH3:9]

Participants

6

Reactant 4

HCID 17324-Chloro-3-methylphenolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chloride

Product 1

HCID 18621211HCID 18621211, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-3-methylphenol (35.0 g, 277 mmol) in 100 mL of methylene chloride at 0° C. was added triethylamine (77.0 mL, 554 mmol), followed by methanesulfonyl chloride (32.2 mL, 416 mmol). The reaction was allowed to warm to room temperature for 1 hr. The solution was poured into EtOAc, washed with H2O and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting yellow solid product was used without further purification.

Workup

  1. washwashed with H2O and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting yellow solid product was used without further purification

Sources & evidence

ORD record
ord-636ec6dd0685410eaf5102d079b4e46d
Source dataset
uspto-grants-2003_03
Patent number
US06534506B2

Reaction notes

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