Cyclopentanol → Cyclopentyl 4-methylbenzene-1-sulfonate

HRID 1684322Notes

Reaction equation

HRID 1684322 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1>N1C=CC=CC=1>[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 7298CyclopentanolHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 317685Cyclopentyl 4-methylbenzene-1-sulfonateYield 80.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A round-bottomed separable flask (3,000 cc) equipped with a mechanical stirrer was charged with cyclopentyl alcohol (500 g, 5.80 mol) and p-toluenesulfonyl chloride (1,210 g, 6.35 mol), followed by the addition of pyridine (2,000 mL) under ice cooling to form a solution. The mixture 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 (3,000 mL) and stirred thoroughly. The precipitating solids were isolated by filtration, washed thoroughly with water and dried to give a white crystal of cyclopentyl p-toluenesulfonate (1,117 g; yield=80.1%). MP: <30° C. 1H-NMR(CDCl3,TMS,ppm): δ1.23-2.07(8H,m), 2.45(3H,s), 4.98(1H,m), 7.38(2H,d,J=9.0Hz), 7.85(2H,d,J=9.0Hz).

Workup

  1. customA round-bottomed separable flask (3,000 cc) equipped with a mechanical stirrer
  2. customto form a solution
  3. customAfter completion of the reaction
  4. stirringstirred thoroughly
  5. customThe precipitating solids were isolated by filtration
  6. washwashed thoroughly with water
  7. customdried

Sources & evidence

ORD record
ord-0e65869db28140b2bb9edde86fd51ad7
Source dataset
uspto-grants-1997_06
Patent number
US05639915

Reaction notes

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