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Sodium Iodide → 2-Methoxy-4-propylphenyl 4-methylbenzenesulfonate

HRID 625990
Notes
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Reaction equation

HRID 625990 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH3:11])[CH:6]=[CH:5][C:4]=1[OH:12].[Na+].[I-].C([O-])([O-])=O.[K+].[K+].[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>C(#N)C>[CH3:28][C:27]1[CH:29]=[CH:30][C:24]([S:21]([O:12][C:4]2[CH:5]=[CH:6][C:7]([CH2:9][CH2:10][CH3:11])=[CH:8][C:3]=2[O:2][CH3:1])(=[O:23])=[O:22])=[CH:25][CH:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 177394-Propylguaiacol

Product 1

HCID 591913892-Methoxy-4-propylphenyl 4-methylbenzenesulfonateYield 66%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-methoxy-4-propylphenol (10.0 mmol; 1.6 mL), NaI (1.0 mmol; 150 mg), and K2CO3 (11.0 mmol; 1.52 g), under argon, in acetonitrile (20 mL) was added tosyl chloride (10.5 mmol; 2.0 g). The reaction mixture was stirred at 70° C. for 36 hr, then quenched with NaOH (0.1N; 3 mL), and extracted with ethyl acetate (2*10 mL). Combined organic phases were washed with saturated NaHCO3 sat. (5 mL), dried over MgSO4, concentrated in vacuo. The crude was chromatographed on silica gel (gradient cyclohexane/dichloromethane) to yield the desired compound as a clear oil (2.13 g; 6.6 mmol; 66%).

Workup

  1. customquenched with NaOH (0.1N; 3 mL)
  2. extractionextracted with ethyl acetate (2*10 mL)
  3. washCombined organic phases were washed with saturated NaHCO3 sat. (5 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude was chromatographed on silica gel (gradient cyclohexane/dichloromethane)

Sources & evidence

ORD record
ord-3cc95fae80bc4f42afe4dcfdc47233ef
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09309179B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes