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

HRID 21482Notes

Reaction equation

HRID 21482 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

3-Methylcyclopentanol (5.0 g, 49.9 mmol) was reacted with p-toluenesulfonyl chloride in pyridine (50 ml) in the same procedure as in Reference Example 7 to obtain 3-methylcyclopentyl p-toluenesulfonate (11.7 g, 46.2 mmol, 92.5% yield). 1H-NMR Spectrum (CDCl3, TMS, ppm): δ0.93 and 1.00 (total 3H, each d, J=6.0 Hz), 1.20-2.30 (7H, m), 2.48 (3H, s), 4.97 (1H, m), 7.38 (1H, d, J=8.0 Hz), 7.85 (1H, d, J=8.0 Hz).

Sources & evidence

ORD record
ord-d1cf6d5c289043e39368c40685424c0b
Source dataset
uspto-grants-1995_06
Patent number
US05424277

Reaction notes

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