Nitric Acid → HCID 21713582, compound

HRID 649748Notes

Reaction equation

HRID 649748 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([S:16]([O-:19])(=[O:18])=[O:17])=[CH:8][CH:7]=1)=[O:4].[K+].[N+:21]([O-])([OH:23])=[O:22]>C(OCC)C>[CH3:1][O:2][C:3]([CH2:5][C:6]1[C:15]2[C:10](=[C:11]([N+:21]([O-:23])=[O:22])[CH:12]=[CH:13][CH:14]=2)[C:9]([S:16]([OH:19])(=[O:18])=[O:17])=[CH:8][CH:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 23717814HCID 23717814, compound

Product 1

HCID 21713582HCID 21713582, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-15 °C

Procedure

Potassium 1-(methoxycarbonylmethyl)-4-naphthalene sulfonate (10 g, 31.4 mmol) was added portionwise over 30 minutes to 90% nitric acid, which was cooled in a methanol/ice bath to approximately −15° C. After 2 hours, the bath temperature had reached −10° C. and diethyl ether (200 mL) was added to the mixture. The precipitated solid was filtered, washed with ether (100 mL) and isopropanol (20 mL), and dried under a stream of nitrogen to give the title compound as an approximately 70:30 mixture of the 5- and 8-nitro isomers (approximately 12 g).

Workup

  1. customhad reached −10° C.
  2. filtrationThe precipitated solid was filtered
  3. washwashed with ether (100 mL) and isopropanol (20 mL)
  4. customdried under a stream of nitrogen

Sources & evidence

ORD record
ord-762fa368271e4ed3b4de59720880dfd4
Source dataset
uspto-grants-2001_08
Patent number
US06271222B1

Reaction notes

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