4-Toluenesulfonyl chloride → 2-(Cyclohexyloxy)ethyl 4-methylbenzene-1-sulfonate

HRID 1058754Notes

Reaction equation

HRID 1058754 reaction equation
[CH:1]1([O:7][CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH:1]1([O:7][CH2:8][CH2:9][O:10][S:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=2)(=[O:19])=[O:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 2247752-(Cyclohexyloxy)ethanol

Product 1

HCID 113809922-(Cyclohexyloxy)ethyl 4-methylbenzene-1-sulfonateYield 54.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 2-(cyclohexyloxy)-1-ethanol (200 mg, 1.39 mmol) in pyridine (10 mL) at 0° C. was added p-toluenesulfonyl chloride (292 mg, 1.53 mmol) portionwise followed by 4-(dimethylamino)pyridine (a few crystals) and the mixture was stirred at room temperature for 16 hours. The solvent was removed in vacuo to give a crude residue that was partitioned between dichloromethane and 2N aqueous hydrochloric acid. The two layers were separated and the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give a yellow oil. This was purified by column chromatography on silica gel, eluting with dichloromethane, to give the title compound (226 mg, 54%) as a yellow oil.

Workup

  1. customThe solvent was removed in vacuo
  2. customto give a crude residue that
  3. customwas partitioned between dichloromethane and 2N aqueous hydrochloric acid
  4. customThe two layers were separated
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a yellow oil
  9. customThis was purified by column chromatography on silica gel
  10. washeluting with dichloromethane

Sources & evidence

ORD record
ord-72bd66fdf765493abee5e5d475a21a6a
Source dataset
uspto-grants-2003_02
Patent number
US06518282B1

Reaction notes

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