ChemicalBook CAS DataBase List 4-Nitrotoluene-2-sulfonic Acid

4-Nitrotoluene-2-sulfonic Acid synthesis

9synthesis methods

Product Name:4-Nitrotoluene-2-sulfonic Acid
CAS Number:121-03-9
Molecular formula:C7H7NO5S
Molecular Weight:217.2

4-Nitrotoluene is sulfonated with 25 % oleum at 60 ℃ and worked up to give a solution of the sodium salt of 2-Methyl-5-nitrobenzenesulfonic acid.

75-84-3 Synthesis

75-84-3
245 suppliers
$10.00/1g

121-02-8 Synthesis

2-Methyl-5-nitrobenzenesulfonyl chloride

121-02-8
163 suppliers
$6.00/1g

121-03-9
265 suppliers
$15.00/25g

Yield:121-03-9 55%

Reaction Conditions:

with pyridine in 1,4-dioxane

Steps:

24 2-Methyl-5-nitro-benzenesulfonic Acid, 2.2-Dimethylpropyl Ester
EXAMPLE 24 2-Methyl-5-nitro-benzenesulfonic Acid, 2.2-Dimethylpropyl Ester Neopentyl alcohol (0.75 g, 8.50 mmol) was added to a solution of commercially available 2-methyl-5-nitro-benzenesulfonyl chloride (1.00 g, 4.20 mmol), pyridine (1.72 mL, 21.2 mmol and anhydrous dioxane (40 mL). A water cooled condenser was attached and the material was heated to reflux. After stirring for two days the mixture was cooled to room temperature and diluted with ethyl acetate (350 mL). The organic layer was washed with water, then 1 N HCl solution, and finally brine. After drying with MgSO4 the solution was concentrated to afford 690 mg of the title compound as a yellow solid.(55%): ¹H-NMR (DMSO-₆) δ8.57 (d, J=2 Hz, 1H), 8.51 (dd, J=8 Hz, 2 Hz, 1H), 7.85 (d, J=8 Hz, 1H), 3.78 (s, 2H), 2.70 (s, 3H), 0.88 (s, 9H); MS (EI): [M+] 287; Anal. Calc. for C₁₂H₁₇NO₅S: C, 50.16; H, 5.96; N, 4.88. Found: C, 49.83; H, 5.69; N, 4.90.

References:

American Home Products Corporation US6355633, 2002, B1

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