Sodium 3-nitrobenzenesulfonate → HCID 22372529, compound

HRID 439684Notes

Reaction equation

HRID 439684 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:38]=[C:39]([C:42]([CH3:45])([CH3:44])[CH3:43])[C:40]=1[OH:41])[C:23]([O:25][CH2:26][CH2:27][N+:28]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([CH3:30])[CH3:29])=[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:42]([C:39]1[CH:38]=[C:22]([CH:21]=[C:20]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:40]=1[OH:41])[C:23]([O:25][CH2:26][CH2:27][N+:28]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([CH3:30])[CH3:29])=[O:24])([CH3:45])([CH3:44])[CH3:43]

Participants

4

Reactant 2

HCID 31389Sodium 3-nitrobenzenesulfonateHCID 15277884HCID 15277884, compound

Product 1

HCID 22372529HCID 22372529, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A solution of 6.75 g (30 mmol) of sodium m-nitrobenzenesulfonate in 50 ml of water was added to a warm solution of 13.44 g (30 mmol) of N-[2-(3,5-di-tert-butyl-4-hydroxybenzoyloxy)ethyl]-N,N-dimethylbenzylammonium chloride prepared as described in Example 1 in 100 ml of water with water rinse. An oily precipitate formed immediately. The aqueous phase was decanted and the gummy residue was washed twice with water. The gum 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 whereupon the gum crystallized. The solid was collected, washed with ligroine and recrystallized from isopropanol. The yield of product was 12.5 g (67.78% of theory); mp=166°-167.5° C. (A change in crystal form occurred at ~155° C.).

Workup

  1. customprepared
  2. washrinse
  3. customAn oily precipitate formed immediately
  4. customThe aqueous phase was decanted
  5. washthe gummy residue was washed twice with water
  6. dissolutionThe gum was dissolved in methylene chloride
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. additionLigroine was added to the
  11. concentrationconcentrate
  12. customdecanted
  13. customcrystallized
  14. customThe solid was collected
  15. washwashed with ligroine
  16. customrecrystallized from isopropanol
  17. customoccurred at ~155° C.

Sources & evidence

ORD record
ord-6c3b21ddc34a42999a46dca4bc0aad67
Source dataset
uspto-grants-1996_05
Patent number
US05516616

Reaction notes

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