4-Toluenesulfonyl chloride → 69628-96-2

HRID 2211860Notes

Reaction equation

HRID 2211860 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[CH2:6][CH2:7][OH:8])([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:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:15])=[O:14]

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 270542-Nitrophenethyl alcohol

Product 1

HCID 56266369628-96-2Yield 92%

Procedure

2-Nitrophenethyl tosylate was prepared according to the general method as outlined in Preparation 1 starting from 2-nitrophenethyl alcohol (15 g, 89.7 mmol) and tosyl chloride (20.52 g, 110 mmol). The residue was triturated with hexanes and 26.44 g of off white crystals were collected. Yield 92%; 1H NMR (400 MHz, CDCl3) δ 7.93 (d, J=9.7 Hz, 1H), 7.91 (d, J=9.7 Hz, 2H), 7.64 (t, 1H), 7.39 (m, 2H), 7.24 (s, 2H), 4.32 (t, J=6 Hz, 2H), 3.24 (t, J=6 Hz, 2H), 2.41 (s, 3H).

Workup

  1. customThe residue was triturated with hexanes and 26.44 g of off white crystals
  2. customwere collected

Sources & evidence

ORD record
ord-4320272dd2a0488e8ef4c36dca39275f
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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