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

HRID 529868Notes

Reaction equation

HRID 529868 reaction equation
[CH:1]1([C:7]2[CH:15]=[C:14]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:13]=[C:12]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:8]=2[C:9]([OH:11])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])O.[Na+:32].C(C(C)=O)C(C)C>O>[CH:22]1([C:12]2[CH:13]=[C:14]([CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)[CH:15]=[C:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:8]=2[C:9]([O-:11])=[O:10])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[Na+:32]

Participants

5

Reactant 3

HCID 7909Methyl Isobutyl KetoneHCID 516892Sodium BicarbonateHCID 898320272,4,6-Tricyclohexylbenzoic acid

Product 1

HCID 118556698Sodium 2,4,6-tricyclohexylbenzoateYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 300-mL eggplant shaped flask was charged with 2.0 g of 2,4,6-tricyclohexylbenzoic acid (prepared in Synthesis Example 1-5), 0.5 g of sodium hydrogencarbonate, 10 g of methyl isobutyl ketone, and 10 g of water, which were stirred at room temperature. At the end of stirring, the reaction solution was concentrated, followed by twice of azeotropic dehydration with 30 g of methyl isobutyl ketone. To the solid precipitate, 30 g of acetonitrile 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-tricyclohexylbenzoate as white crystal. Amount 2.0 g, yield 90%.

Workup

  1. stirringAt the end of stirring
  2. concentrationthe reaction solution was concentrated
  3. additionTo the solid precipitate, 30 g of acetonitrile was added, whereupon solid-liquid
  4. washwashing
  5. filtrationThe solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-3fabc2403c284e64b8b5bb7dc2ff6aec
Source dataset
uspto-grants-2016_05
Patent number
US09348227B2

Reaction notes

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