Sodium Tetraphenylborate → HCID 22372527, compound

HRID 439685Notes

Reaction equation

HRID 439685 reaction equation
[C:1]1([B-:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[Cl-].[C:28]([C:32]1[CH:33]=[C:34]([CH:50]=[C:51]([C:54]([CH3:57])([CH3:56])[CH3:55])[C:52]=1[OH:53])[C:35]([O:37][CH2:38][CH2:39][N+:40]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([CH3:42])[CH3:41])=[O:36])([CH3:31])([CH3:30])[CH3:29]>O>[C:20]1([B-:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1.[C:54]([C:51]1[CH:50]=[C:34]([CH:33]=[C:32]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:52]=1[OH:53])[C:35]([O:37][CH2:38][CH2:39][N+:40]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([CH3:42])[CH3:41])=[O:36])([CH3:57])([CH3:56])[CH3:55]

Participants

4

Reactant 2

HCID 2723787Sodium TetraphenylborateHCID 15277884HCID 15277884, compound

Product 1

HCID 22372527HCID 22372527, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A solution of 10.27 g (30 mmol) of sodium tetraphenylborate in 70 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. A solid precipitate formed on cooling and 100 ml of water was added to the mixture after which the solid was collected, washed with water and dissolved in methylene chloride. The water layer was separated and the methylene chloride layer was dried over magnesium sulfate and concentrated. The solid was collected, recrystallized from ethyl acetate and dried. The yield of product was 9.16 g (41.7% of theory); mp=213°-214° C.

Workup

  1. customprepared
  2. customA solid precipitate formed
  3. temperatureon cooling
  4. customwas collected
  5. washwashed with water
  6. dissolutiondissolved in methylene chloride
  7. customThe water layer was separated
  8. dry with materialthe methylene chloride layer was dried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe solid was collected
  11. customrecrystallized from ethyl acetate
  12. customdried

Sources & evidence

ORD record
ord-b81fd7246a764b7b8e553f019f0e8699
Source dataset
uspto-grants-1996_05
Patent number
US05516616

Reaction notes

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