Methyl Isobutyl Ketone → Sodium 2,4,6-triisopropylbenzoate

HRID 529864Notes

Reaction equation

HRID 529864 reaction equation
[CH:1]([C:4]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:10]=[C:9]([CH:16]([CH3:18])[CH3:17])[C:5]=1[C:6]([OH:8])=[O:7])([CH3:3])[CH3:2].C(=O)([O-])O.[Na+:23].C(C(C)=O)C(C)C>O>[CH:1]([C:4]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:10]=[C:9]([CH:16]([CH3:18])[CH3:17])[C:5]=1[C:6]([O-:8])=[O:7])([CH3:3])[CH3:2].[Na+:23]

Participants

5

Reactant 3

HCID 7909Methyl Isobutyl KetoneHCID 962142,4,6-Tris(1-methylethyl)benzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 118556701Sodium 2,4,6-triisopropylbenzoateYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1-L eggplant shaped flask was charged with 39.7 g of 2,4,6-triisopropylbenzoic acid (prepared in Synthesis Example 1-1), 13.4 g of sodium hydrogencarbonate, 160 g of methyl isobutyl ketone, and 40 g of water, which were stirred at room temperature for 24 hours. At the end of stirring, the reaction solution was concentrated, followed by twice of azeotropic dehydration with 100 g of methyl isobutyl ketone. To the solid precipitate, 300 g of diisopropyl ether was added, whereupon solid-liquid washing was conducted for 30 minutes. The solid was filtered and dried, obtaining the target compound, sodium 2,4,6-triisopropylbenzoate as white crystal. Amount 30.7 g, yield 80%.

Workup

  1. stirringAt the end of stirring
  2. concentrationthe reaction solution was concentrated
  3. additionTo the solid precipitate, 300 g of diisopropyl ether was added, whereupon solid-liquid
  4. washwashing
  5. waitwas conducted for 30 minutes
  6. filtrationThe solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-33ce6d07f13d44beaf73a2e66db329e9
Source dataset
uspto-grants-2016_05
Patent number
US09348227B2

Reaction notes

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