Isovaleric Acid → HCID 54269023, compound

HRID 1526670Notes

Reaction equation

HRID 1526670 reaction equation
[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:29])[C@@H:13]([OH:28])[CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][C@@H:23]([OH:25])[CH2:24][C@H:19]4[CH2:18][C@@H:17]([OH:27])[C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5](O)=O.[C:30](O)(=O)[CH2:31][CH:32](C)C.C[O-].[Na+]>CO.[Pt]>[OH:25][C@@H:23]1[CH2:22][CH2:21][C@@:20]2([CH3:26])[CH:19]([CH2:18][C@@H:17]([OH:27])[C@@H:16]3[C@@H:15]2[CH2:14][C@H:13]([OH:28])[C@@:12]2([CH3:29])[C@H:11]3[CH2:10][CH2:9][C@@H:8]2[C@H:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH:31]([CH3:32])[CH3:30])[CH2:24]1

Participants

6

Reactant 3

HCID 10430Isovaleric AcidHCID 221493Cholic AcidHCID 10942334Sodium Methoxide

Product 1

HCID 54269023HCID 54269023, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

The product was synthesized by the electrochemical oxidative decarboxylation of carboxylic acids (Kolbe electrolysis) according to a literature procedure (Bergström, S. and Krabisch, L., Acta Chem. Scand. 1957, 11, 1067). To a solution of cholic acid (10 g, 24.5 mmol) and isovaleric acid (70 mL, 644 mmol) in methanol (400 mL) was added sodium methoxide (2.5 g). The solution was placed in a beaker surrounded by ice. The electrolysis was run for 24 hours with 1.0 A between platinum electrodes. After work up, the product was crystallized from acetone (6.2 g, 60%).

Workup

  1. customAfter work up, the product was crystallized from acetone (6.2 g, 60%)

Sources & evidence

ORD record
ord-46e56be178834725a034e79308b7db8d
Source dataset
uspto-grants-2015_07
Patent number
US09085602B1

Reaction notes

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