4-Toluenesulfonyl chloride → 3-Methyl-2-nitrophenethyl tosylate

HRID 2211883Notes

Reaction equation

HRID 2211883 reaction equation
[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][CH2:6][OH:7].[S:14](Cl)([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15]>>[S:14]([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)([O:7][CH2:6][CH2:5][C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([CH3:1])[C:3]=1[N+:11]([O-:13])=[O:12])(=[O:16])=[O:15]

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 136636522-(3-Methyl-2-nitrophenyl)ethan-1-ol

Product 1

HCID 219632193-Methyl-2-nitrophenethyl tosylateYield 100%

Procedure

3-Methyl-2-nitrophenethyl tosylate was prepared according to the general method as outlined in Preparation 1 starting from 3-methyl-2-nitrophenethyl alcohol (1.06 g, 5.86 mmol) and tosyl chloride (1.34 g, 7 mmol). 2 g product was taken crude to the next step. Yield 100%; 1H NMR (400 MHz, CDCl3) δ 7.68 (d, 2H), 7.29 (m, 3H), 7.17 (t, 2H), 4.23 (t, J=6 Hz, 2H), 2.89 (t, J=6 Hz, 2H), 2.42 (s, 3H), 2.27 (s, 3H).

Sources & evidence

ORD record
ord-76b5effc3b0b4c6ead51b8961faacf96
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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