Toluene → (3-Ethyloxetan-3-yl)methyl 4-methylbenzenesulfonate

HRID 888313Notes

Reaction equation

HRID 888313 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[OH-].[Na+].[CH2:21]([C:23]1([CH2:27][OH:28])[CH2:26][O:25][CH2:24]1)[CH3:22]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[CH2:21]([C:23]1([CH2:27][O:28][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:26][O:25][CH2:24]1)[CH3:22]

Participants

7

Reactant 4

HCID 1140Toluene2×HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 76444Oxt-101

Product 1

HCID 11425703(3-Ethyloxetan-3-yl)methyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

After adding p-toluene sulfonyl chloride (229 g (1.2 mol)), benzyltriethylammonium chloride (17.1 g (75 mmol)) and toluene (450 ml) to a glass flask of an inner volume of 2,000 ml equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser, while keeping the liquid temperature below 5° C., a 35% aqueous sodium hydroxide solution (200 g (1.75 mol)) was gradually added. While keeping the liquid temperature below 10° C., 3-ethyl-3-hydroxymethyloxetane (116.2 g (1.0 mol)) was dropwise added to perform the reaction at the same temperature for 1 hour and at room temperature for 5 hours. After the completion of the reaction, toluene (150 ml) and water (250 ml) were added to a reaction solution and a liquid separation was performed. After washing a resultant organic layer with water (250 ml) twice, a magnesium sulphate was added so that the organic layer was dried. After the completion of drying, the organic layer was filtered and a resultant filtrate was concentrated under reduced pressure to give, as a colorless liquid, 3-ethyl-3-p-toluene sulfonyloxymethyloxetane having a purity of 90% (a value measured by 1H-NMR) (285 g) (an isolated yield based on 3-ethyl-3-hydroxymethyloxetane standard: 95%).

Workup

  1. customequipped with a stirrer
  2. customthe liquid temperature below 5° C.
  3. additionwas dropwise added
  4. customthe reaction at the same temperature for 1 hour
  5. additionwere added to a reaction solution
  6. customa liquid separation
  7. washAfter washing a resultant organic layer with water (250 ml) twice
  8. additiona magnesium sulphate was added so that the organic layer
  9. customwas dried
  10. customAfter the completion of drying
  11. filtrationthe organic layer was filtered
  12. concentrationa resultant filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b43b5212235b4b75a73e39dd93961adf
Source dataset
uspto-grants-2012_08
Patent number
US08247583B2

Reaction notes

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