4-Toluenesulfonyl chloride → 4-Nitrophenethyl tosylate

HRID 2211856Notes

Reaction equation

[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[S:20](Cl)([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>C(Cl)Cl>[S:20]([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)([O:10][CH2:9][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=1)(=[O:22])=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

4-Nitrophenethyl alcohol (15 g, 89.7 mmol) was dissolved in 450 mL methylene chloride. Triethylamine (37.5 mL, 269 mmol) was added over 10 min and the reaction mixture was stirred at 0° C. for 1 hour (h). Tosyl chloride (20.52 g, 110 mmol) was added slowly to the mixture at 0° C. The reaction was stirred at room temperature (rt) overnight and was concentrated. The residue was dissolved in methylene chloride and washed with water, 1 N HCl, then water. The organic layer was dried over sodium sulfate and evaporated. The residue was triturated with hexanes and 25.32 g of white solid was collected. Yield 88%; 1H NMR (400 MHz, CDCl3) δ 8.07 (d, J=8 Hz, 2H), 7.63 (d, J=8 Hz, 2H), 7.24 (d, 4H), 4.26 (t, J=6 Hz, 2H), 3.04 (t, J=6 Hz, 2H), 2.41 (s, 3H).

Workup

stirringThe reaction was stirred at room temperature (rt) overnight
concentrationwas concentrated
dissolutionThe residue was dissolved in methylene chloride
washwashed with water, 1 N HCl
dry with materialThe organic layer was dried over sodium sulfate
customevaporated
customThe residue was triturated with hexanes and 25.32 g of white solid
customwas collected

Sources & evidence

ORD record: ord-a4212b9624f64ac4a1f9fff7655ebd1e
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101886B2

Reaction notes

Loading…