Nitric Acid → HCID 22457564, compound

Temperature

-20 °C

4-(2-Acetoxy-ethyl)-naphthalene-1-sulfonyl chloride (76.96 g, 246 mmol) was added portionwise over 12 minutes to 90% nitric acid (154 mL, 3.278 mol) cooled in an ice-methanol bath (−20° C.). After the addition was complete, the reaction mixture was stirred at −20° C. for an additional 15 minutes. The reaction mixture was partitioned between ice water (800 mL) and chloroform (800 mL). The aqueous layer was extracted with chloroform (100 mL). The combined organic layers were washed with brine (400 mL, 200 mL), then dried over magnesium sulfate, filtered, and evaporated to a golden oil. Diethyl ether (300 mL) was added to the crude product and the mixture was shaken vigorously to afford an off-white solid. The solid was collected by filtration, washed with ether (2×50 mL), and dried under vacuum to afford 4-(2-acetoxy-ethyl)-8-nitro-naphthalene-1-sulfonyl chloride (41.85 g) as an off-white solid.

1. additionAfter the addition
2. customThe reaction mixture was partitioned between ice water (800 mL) and chloroform (800 mL)
3. extractionThe aqueous layer was extracted with chloroform (100 mL)
4. washThe combined organic layers were washed with brine (400 mL, 200 mL)
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. customevaporated to a golden oil
8. additionDiethyl ether (300 mL) was added to the crude product
9. stirringthe mixture was shaken vigorously
10. customto afford an off-white solid
11. filtrationThe solid was collected by filtration
12. washwashed with ether (2×50 mL)
13. customdried under vacuum

ORD record

ord-e98d9f5191a04a2ca063d4d47b2b0499

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06399597B1