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Sodium Acetate → 2,2-Dimethyl-5-ethyl-5-formyl-1,3-dioxane

HRID 704137
Notes
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Reaction equation

HRID 704137 reaction equation
[CH3:1][C:2]1([CH3:12])[O:7][CH2:6][C:5]([CH2:10][CH3:11])([CH2:8][OH:9])[CH2:4][O:3]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+]>ClCCl.CCOCC>[CH3:1][C:2]1([CH3:12])[O:3][CH2:4][C:5]([CH2:10][CH3:11])([CH:8]=[O:9])[CH2:6][O:7]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 118161521,3-Dioxane-5-methanol, 5-ethyl-2,2-dimethyl-HCID 178418287HCID 178418287, compound

Product 1

HCID 120128162,2-Dimethyl-5-ethyl-5-formyl-1,3-dioxaneYield 92%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

2,2-Dimethyl-5-ethyl-5-hydroxymethyl-1,3-dioxane (33 g.) was added to a stirred suspension of pyridinium chlorochromate (122.6 g) and anhydrous sodium acetate (7.8 g.) in dry dichloromethane (200 ml.), at 0°, under a current of nitrogen. The mixture was stirred at room temperature for six hours. The mixture was diluted with dry ether (500 ml) and the organic solution was decanted off. The oily residue was treated with ether and the combined extracts were evaporated in vacuo. The residue was purified by chromatography on silica, eluting with ether: hexane 1:3. 2,2-Dimethyl-5-ethyl-5-formyl-1,3-dioxane (30 g.) was obtained as a colourless oil.

Workup

  1. customthe organic solution was decanted off
  2. additionThe oily residue was treated with ether
  3. customthe combined extracts were evaporated in vacuo
  4. customThe residue was purified by chromatography on silica
  5. washeluting with ether: hexane 1:3

Sources & evidence

ORD record
ord-7ab9d0024105477a8aa63b1591117185
Source dataset
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04985582

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes