Triethylamine → Retinal

HRID 346881

Reaction equation

HRID 346881 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[CH2:14][CH2:13][CH2:12][C:11]([CH3:16])([CH3:15])[C:10]=1/[CH:17]=[CH:18]/[C:19](/[CH3:28])=[CH:20]/[CH:21]=[CH:22]/[C:23](/[CH3:27])=[CH:24]/[CH2:25][OH:26].CCCCCC.C(OCC)C>ClCCl>[CH3:8][C:9]1[CH2:14][CH2:13][CH2:12][C:11]([CH3:15])([CH3:16])[C:10]=1/[CH:17]=[CH:18]/[C:19](/[CH3:28])=[CH:20]/[CH:21]=[CH:22]/[C:23](/[CH3:27])=[CH:24]/[CH:25]=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 445354RetinolHCID 21584099Diethylether hexane

Product 1

HCID 638015RetinalYield 152.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Retinol anhydride (1.00 g, 0.0017 mol) and triethylamine (0.31 g, 0.0021 mol) were added to retinol (0.60 g, 0.0021 mol) dissolved in anhydrous dichloromethane (30 ml) at 0° C. The reaction solution was slowly warmed to room temperature and stirred for 5 hours under nitrogen atmosphere and under the condition for light and moisture to be intercepted. The reaction solution was filtered and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (silica gel 60 for cc part, Merk Co., mesh size 270–400, hexane/diethylether=9/1, v/v) to give 0.91 g (Yield 92%) of the pale yellow title compound. 1H NMR data of this compound were the same as those in Example 1.

Workup

  1. filtrationThe reaction solution was filtered
  2. customthe solvent was removed by distillation under reduced pressure
  3. customThe residue was purified by column chromatography (silica gel 60 for cc part, Merk Co

Sources & evidence

ORD record
ord-4e6bd1bee73a46ee881868e8d3871b22
Source dataset
uspto-grants-2007_02
Patent number
US07173062B2

Linked notes

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