Sodium 3-nitrobenzenesulfonate → HCID 22372532, compound

HRID 439688Notes

Reaction equation

HRID 439688 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([O-:13])(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Na+].[Cl-].[C:16]([C:20]1[CH:21]=[C:22]([CH:39]=[C:40]([C:43]([CH3:46])([CH3:45])[CH3:44])[C:41]=1[OH:42])[C:23]([O:25][CH2:26][CH2:27][CH2:28][N+:29]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([CH3:31])[CH3:30])=[O:24])([CH3:19])([CH3:18])[CH3:17]>O>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([O-:13])(=[O:11])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:43]([C:40]1[CH:39]=[C:22]([CH:21]=[C:20]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:41]=1[OH:42])[C:23]([O:25][CH2:26][CH2:27][CH2:28][N+:29]([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)([CH3:31])[CH3:30])=[O:24])([CH3:45])([CH3:46])[CH3:44]

Participants

4

Reactant 2

HCID 31389Sodium 3-nitrobenzenesulfonateHCID 22372525HCID 22372525, compound

Product 1

HCID 22372532HCID 22372532, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 10.27 g (30 mmol) of sodium m-nitrobenzenesulfonate in 70 ml of water was added to a hot solution of 13.86 g (30 mmol) of N-[3-(3,5-di-tert-butyl-4-hydroxybenzoyloxy)propyl]-N,N-dimethylbenzylammonium chloride prepared as described in Example 4 in 100 ml of water. An oily precipate formed. The aqueous phase was decanted and the residue was dissolved in methylene chloride, washed with water, dried over magnesium sulfate and concentrated. Ligroine was added to the concentrate and decanted followed by hot heptane treatment. The residue was dissolved in methylene chloride and concentrated to a white solid. The yield of N-[3-(3,5-di-tert-butyl-4-hydroxybenzoyloxy)propyl]-N,N-dimethylbenzylammonium m-nitrobenzene sulfonate was 10.5 g (55.6% of theory).

Workup

  1. customprepared
  2. customAn oily precipate formed
  3. customThe aqueous phase was decanted
  4. dissolutionthe residue was dissolved in methylene chloride
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. additionLigroine was added to the
  9. concentrationconcentrate
  10. customdecanted
  11. dissolutionThe residue was dissolved in methylene chloride
  12. concentrationconcentrated to a white solid

Sources & evidence

ORD record
ord-78ef1ed9e02a4fe391d439679f0e7843
Source dataset
uspto-grants-1996_05
Patent number
US05516616

Reaction notes

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