Water → 2-(Cyclohex-2-enyloxy)ethyl 4-methylbenzenesulfonate

HRID 425072Notes

Reaction equation

HRID 425072 reaction equation
[CH:1]1([O:7][CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[S:11](Cl)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12].O>N1C=CC=CC=1>[CH3:18][C:17]1[CH:19]=[CH:20][C:14]([S:11]([O:10][CH2:9][CH2:8][O:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]2)(=[O:13])=[O:12])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 112865262-(Cyclohex-2-enyloxy)ethanol

Product 1

HCID 576846852-(Cyclohex-2-enyloxy)ethyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 2-(cyclohex-2-enyloxy)ethanol (intermediate BU) (0.3 g) in anhydrous pyridine was added TsCl (1.3 eq). The mixture was stirred at room temperature for 16 h, after which TLC showed the reaction was complete. The mixture was poured into water, extracted with EA, washed with water and brine, and dried with anhydrous Na2SO4. Solvent was removed and the residue purified by column chromatography to obtain intermediate BV (0.3 g).

Workup

  1. extractionextracted with EA
  2. washwashed with water and brine
  3. dry with materialdried with anhydrous Na2SO4
  4. customSolvent was removed
  5. customthe residue purified by column chromatography
  6. customto obtain intermediate BV (0.3 g)

Sources & evidence

ORD record
ord-b6ffbf4bd3444a939396521c71931968
Source dataset
uspto-grants-2012_01
Patent number
US08106021B2

Reaction notes

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