Hydrochloric Acid → 4-Methyl-3-nitrobenzyl methanesulfonate
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].Cl>C(Cl)Cl.CCCCCC.C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][S:21]([CH3:20])(=[O:23])=[O:22])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]Participants
Procedure
(4-Methyl-3-nitro-phenyl)-methanol (3.00 g, 17.95 mmol) was taken up in anhydrous DCM, under argon, and triethyl amine (5.45 g, 53.85 mmol, 7.51 mL) was added. The solution was cooled to 0EC and methanesulfonyl chloride (2.26 g, 19.74 mmol, 1.53 mL) was added slowly via syringe. The solution was allowed to warm to room temp and stir for 12 h. The reaction mixture poured into 1N HCl and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with water, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (5:1 hexane/ethyl acetate) Yield 2.00 g. 1H NMR (CDCl3, 300 MHz): δ 2.62 (s, 3H), 4.61 (s, 2H), 7.36 (d, J=8 Hz, 1H), 7.36 (d, J=8 Hz, 1H), 8.02 (s, 1H).
Workup
- additionwas added slowly via syringe
- extractionthe aqueous layer was extracted three times with ethyl acetate
- washThe combined organic layers were washed with water, brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationThe solution was filtered
- customthe solvent removed under reduced pressure
- customThe product was isolated by flash chromatography
Sources & evidence
- ORD record
- ord-39a2119422e244269afe4d3a985821bb
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07479495B2
Reaction notes
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