4-Toluenesulfonyl chloride → 3-Nitrophenethyl tosylate

HRID 2211862Notes

Reaction equation

HRID 2211862 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7][CH2:8][OH:9])([O-:3])=[O:2].[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14]>>[S:13]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)([O:9][CH2:8][CH2:7][C:6]1[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:15])=[O:14]

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 1040583-Nitrophenylethyl alcohol

Product 1

HCID 123638823-Nitrophenethyl tosylateYield 96%

Procedure

3-Nitrophenethyl tosylate was prepared according to the general method as outlined in Preparation 1 starting from 3-nitrophenethyl alcohol (15 g, 89.7 mmol) and tosyl chloride (20.52 g, 110 mmol). The product was isolated as an off white powder (21.5 g). Yield 96%; 1H NMR (400 MHz, CDCl3) δ 8.06 (d, 1H), 7.87 (t, 1H), 7.63 (d, 2H), 7.46 (m, 2H), 7.25 (m, 2H), 4.26 (t, J=6 Hz, 2H), 3.04 (t, J=6 Hz, 2H), 2.40 (s, 3H).

Sources & evidence

ORD record
ord-f2d220fa21bf4988871894bafc8df65e
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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