Water → Sodium oleanolate

HRID 580310Notes

Reaction equation

HRID 580310 reaction equation
[OH-].[Na+:2].[CH3:3][C@@:4]12[C@H:13]3[CH2:14][CH:15]=[C:16]4[C@@H:21]5[CH2:22][C:23]([CH3:27])([CH3:26])[CH2:24][CH2:25][C@:20]5([C:28]([OH:30])=[O:29])[CH2:19][CH2:18][C@@:17]4([CH3:31])[C@:12]3([CH3:32])[CH2:11][CH2:10][C@H:9]1[C:8]([CH3:34])([CH3:33])[C@@H:7]([OH:35])[CH2:6][CH2:5]2.O.ClCCl>C(OCC)C>[CH3:3][C@@:4]12[C@H:13]3[CH2:14][CH:15]=[C:16]4[C@@H:21]5[CH2:22][C:23]([CH3:26])([CH3:27])[CH2:24][CH2:25][C@:20]5([C:28]([O-:30])=[O:29])[CH2:19][CH2:18][C@@:17]4([CH3:31])[C@:12]3([CH3:32])[CH2:11][CH2:10][C@H:9]1[C:8]([CH3:34])([CH3:33])[C@@H:7]([OH:35])[CH2:6][CH2:5]2.[Na+:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 10494Oleanolic Acid3×HCID 14798Sodium Hydroxide4×

Product 1

HCID 49857633Sodium oleanolate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 10% aqueous solution of sodium hydroxide is added to an almost saturated solution of oleanolic acid in a water immiscible solvent, for example dichloromethane or diethyl ether. The volume of the sodium hydroxide solution is controlled by the amount of oleanolic acid taken; the final mixture should contain at least one, preferably 1,5 to 3, mole sodium hydroxide per mole oleanolic acid--a large excess of the sodium hydroxide solution may lower the yield. The mixture is mixed well (vigorous stirring or shaking) and the precipitated sodium oleanolate is separated. The sodium oleanolate can be recrystallised from aqueous organic solvents, preferably aqueous methanol or aqueous ethanol.

Workup

  1. additionThe mixture is mixed well
  2. customthe precipitated sodium oleanolate is separated
  3. customThe sodium oleanolate can be recrystallised from aqueous organic solvents, preferably aqueous methanol or aqueous ethanol

Sources & evidence

ORD record
ord-72e40d7f526c429e96875cde66ff49b2
Source dataset
uspto-grants-1988_06
Patent number
US04752606

Reaction notes

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