تفاعل #364762

معادلة التفاعل

Neopentyl alcohol

2-methyl-5-nitro-benzenesulfonyl chloride

pyridine

dioxane

→

title compound

المردود 57.2%

2-Methyl-5-nitro-benzenesulfonic Acid, 2.2-Dimethylpropyl Ester

المردود 57.2%

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   أخرىA water cooled condenser was attached
2. 2
   درجة الحرارةthe material was heated to reflux
3. 3
   غسيلThe organic layer was washed with water
4. 4
   تجفيفAfter drying with MgSO4 the solution
5. 5
   تركيزwas concentrated

الإجراء التجريبي

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%): 1HNMR (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.

المصدر