Cyclopentanol → Cyclopentyl 4-methylbenzene-1-sulfonate

HRID 21480

Reaction equation

HRID 21480 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 68.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Cyclopentanol (50.0 g, 0.58 mol) and p-toluenesulfonyl chloride (120 g, 0.629 mol) were dissolved in pyridine (200 ml), and the solution was poured into ice-water (about 1 liter), followed by thoroughly stirring. The precipitated solid was filtered and dried to obtain cyclopentyl p-toluenesulfonate as a white solid (94.9 g, 0.390 mol, 68.1% yield).

Workup

  1. filtrationThe precipitated solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-7763fe572c454ab3929f14c2186a331a
Source dataset
uspto-grants-1995_06
Patent number
US05424277

Linked notes

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