Water → 4-Methoxy-5-methyl-2-nitrophenyl 4-methylbenzenesulfonate

HRID 337365Notes

Reaction equation

HRID 337365 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([OH:10])=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.C(N(CC)CC)C.O>C(Cl)Cl>[CH3:24][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O:10][C:6]2[CH:7]=[C:8]([CH3:9])[C:3]([O:2][CH3:1])=[CH:4][C:5]=2[N+:11]([O-:13])=[O:12])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 574186644-Methoxy-5-methyl-2-nitrophenol

Product 1

HCID 867032684-Methoxy-5-methyl-2-nitrophenyl 4-methylbenzenesulfonateYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-methoxy-5-methyl-2-nitro phenol (8.0 g) in methylene chloride (80 mL) was added p-toluenesulfonyl chloride (9.15 g) at room temperature under nitrogen atmosphere. The mixture was cooled to 0° C. To this mixture triethylamine (4.86 g) was added and stirred for 2 h. Then the reaction mixture was poured into water (150 mL) and extracted with methylene chloride (150 mL). The organic layer was washed with water (100 mL) and saturated brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using hexane/ethyl acetate (9:1) to give the title compound (12.0 g).

Workup

  1. extractionextracted with methylene chloride (150 mL)
  2. washThe organic layer was washed with water (100 mL) and saturated brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-4e7cff8f2e564713a42a9ab76bfbd568
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Reaction notes

Loading…