4-Toluenesulfonyl chloride → 3-Methylcyclopentyl 4-methylbenzene-1-sulfonate

HRID 1684325Notes

Reaction equation

HRID 1684325 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3]1.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>N1C=CC=CC=1>[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([O:7][CH:4]2[CH2:5][CH2:6][CH:2]([CH3:1])[CH2:3]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 867853-Methylcyclopentan-1-ol

Product 1

HCID 190423383-Methylcyclopentyl 4-methylbenzene-1-sulfonateYield 92.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A round-bottomed flask (100 cc) was charged with 3-methylcyclopentyl alcohol (5.0 g, 49.9 mmol) and p-toluenesulfonyl chloride (10.0 g, 52.5 mmol), followed by the addition of pyridine (50 mL) under ice cooling to form a solution. The solution was stirred for 8 h as it was warmed gradually to room temperature. After completion of the reaction, the reaction mixture was poured into ice water and stirred thoroughly. After extraction with ether (100 mL×2), the organic layers were washed with 2N HCl, water and saturated brine, and dried with anhydrous magnesium sulfate. After the desiccant was removed, the solvent was distilled off under vacuum to give 3-methylcyclopentyl p-toluenesulfonate as a colorless clear oil (11.7 g; yield=92.5%). MP: <30° C. 1H-NMR(CDCl3,TMS,ppm): δ0.93 and 1.00(total 3H, each d,J=6.0Hz), 1.20-2.30(7H,m), 2.48(3H,s), 4.97(1H,m), 7.38(2H,d,J=8.0Hz), 7.85(2H,d,J=8.0Hz).

Workup

  1. customto form a solution
  2. customAfter completion of the reaction
  3. stirringstirred thoroughly
  4. extractionAfter extraction with ether (100 mL×2)
  5. washthe organic layers were washed with 2N HCl, water and saturated brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customAfter the desiccant was removed
  8. distillationthe solvent was distilled off under vacuum

Sources & evidence

ORD record
ord-7dac14feabf24f30a2a673feb0a9217c
Source dataset
uspto-grants-1997_06
Patent number
US05639915

Reaction notes

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