Benzyl Chloride → Benzyl-p-toluenethiosulfonate

HRID 481872Notes

Reaction equation

HRID 481872 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:9]([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)([O-:12])(=[O:11])=[S:10].[K+]>C(O)C.CCCCCC>[CH2:1]([O:12][S:9]([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[S:10])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7503Benzyl ChlorideHCID 23662126Benzenesulfonothioic acid, 4-methyl-, potassium salt

Product 1

HCID 54123251Benzyl-p-toluenethiosulfonateYield 77.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

The title compound was prepared as described in General Method 2 using 0.05 mol of benzyl chloride, 0.05 moles of potassium thiotosylate in 150 mL of ethanol. The residue was dissolved in hexane and seeded with a crystal of the product to afford 10.8 g (77%) of benzyl-p-toluenethiosulfonate (m.p. 52°-56.5° C.). 1H NMR (CDCl3) δ2.45 (s, 3H), 4.26 (s, 2H), 7.18-7.30 (m, 7H), 7.74 (d, 2H).

Sources & evidence

ORD record
ord-147c7584ae834adea550cec5cfa92cd2
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

Loading…