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

HRID 1175261Notes

Reaction equation

HRID 1175261 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-d32edab580894e7bafe8ae63e994b0a4
Source dataset
uspto-grants-2010_11
Patent number
US07838499B2

Reaction notes

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