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

HRID 488152Notes

Reaction equation

HRID 488152 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-38b575bca1d94ac9b544ec23065db09a
Source dataset
uspto-grants-1994_03
Patent number
US05298655

Reaction notes

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