Sodium Acetate → 2-Benzyloxymethyl-2-ethyl-propandial

HRID 2372422Notes

Reaction equation

HRID 2372422 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([CH2:15][OH:16])([CH2:13][CH3:14])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+]>ClCCl.CCOCC>[CH2:1]([O:8][CH2:9][C:10]([CH2:13][CH3:14])([CH:15]=[O:16])[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 538066302-((Benzyloxy)methyl)-2-ethylpropane-1,3-diolHCID 178418287HCID 178418287, compound

Product 1

HCID 536976632-Benzyloxymethyl-2-ethyl-propandial

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

2-Benzyloxymethyl-2-hydroxymethyl-butan-1ol (9.7 g.) was added to a stirred suspension of pyridinium chlorochromate (9.7 g.) and anhydrous sodium acetate (2.0 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 (200 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 1:2 ether:hexane. 2-Benzyloxymethyl-2-ethyl-propandial was obtained as a pale brown oil (3.3 g.) and was used immediately.

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 1:2 ether

Sources & evidence

ORD record
ord-359be6eefd3747ee80cd82ddc88d5438
Source dataset
uspto-grants-1992_03
Patent number
US05098929

Reaction notes

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