Sodium Hydroxide → 3-Hydroxy-7,11,15-trimethylhexadeca-6,10,14-trienoic acid

HRID 2379523Notes

Reaction equation

HRID 2379523 reaction equation
[OH:1][CH:2]([CH2:8][CH2:9][CH:10]=[C:11]([CH3:23])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:22])[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[CH2:3][C:4]([O:6]C)=[O:5].[OH-].[Na+]>C(O)C>[OH:1][CH:2]([CH2:8][CH2:9][CH:10]=[C:11]([CH3:23])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:22])[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[CH2:3][C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53652710Methyl 3-hydroxy-7,11,15-trimethylhexadeca-6,10,14-trienoate

Product 1

HCID 537523723-Hydroxy-7,11,15-trimethylhexadeca-6,10,14-trienoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 3-hydroxy-7,11,15-trimethylhexadeca-6,10,14-trienoate (139 mg, 430 μmol), ethanol (1 mL) and sodium hydroxide (1N, 440 μL, 440 μmol) was stirred at room temperature for two-hours. The crude mixture was purified by flash chromatography on a 20 mm ID silica gel column. Elution of the column with choloform:acetic acid (40:1/v=v) gave title compound as a colorless gum.

Workup

  1. customThe crude mixture was purified by flash chromatography on a 20 mm ID silica gel column
  2. washElution of the column with choloform

Sources & evidence

ORD record
ord-d849200d1f1a4eb3b0e88577e2a46dbb
Source dataset
uspto-grants-1994_11
Patent number
US05362906

Reaction notes

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