Nitric Acid → Toluene-4-sulfonic acid 2-isopropyl-4-methoxy-5-nitro-phenyl ester

HRID 925166Notes

Reaction equation

HRID 925166 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[O:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14])([CH3:3])[CH3:2].[N+:23]([O-])([OH:25])=[O:24]>CC(O)=O>[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([N+:23]([O-:25])=[O:24])=[CH:6][C:5]=1[O:12][S:13]([C:16]1[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=1)(=[O:15])=[O:14])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 44248852Toluene-4-sulfonic acid 2-isopropyl-4-methoxy-phenyl ester

Product 1

HCID 59598687Toluene-4-sulfonic acid 2-isopropyl-4-methoxy-5-nitro-phenyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of toluene-4-sulfonic acid 2-isopropyl-4-methoxy-phenyl ester (19.00 g, 59 mmol) in 118 mL AcOH was added 236 ml fuming HNO3 over 20 min. After 16 h the solution was pouring into a rapidly stirring slurry of 21 of ice/H2O. After 15 min the precipitate was filtered, washed with H2O and dried under vacuum (50° C.) to give toluene-4-sulfonic acid 2-isopropyl-4-methoxy-5-nitro-phenyl ester (21.27 g, 98%) and toluene-4-sulfonic acid 2-isopropyl-4-methoxy-3-nitro-phenyl ester and as a pale yellow solid (7:1 inseparable mixture).

Workup

  1. customover 20 min
  2. additionAfter 16 h the solution was pouring into
  3. filtrationAfter 15 min the precipitate was filtered
  4. washwashed with H2O
  5. customdried under vacuum (50° C.)

Sources & evidence

ORD record
ord-ad982c60aeaa4d90b6a9c116901af7f3
Source dataset
uspto-grants-2016_03
Patent number
US09284279B2

Reaction notes

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