Diethyl Ether → [(4S)-2,2,4-Trimethyl-1,3-dioxolan-4-yl]acetaldehyde

HRID 224736Notes

Reaction equation

HRID 224736 reaction equation
[CH3:1][C:2]1([CH3:11])[O:6][C@@:5]([CH3:10])([CH2:7][CH2:8][OH:9])[CH2:4][O:3]1.[Cr](Cl)(O)(=O)=O.N1C=CC=CC=1.CCOCC>C(Cl)Cl>[CH3:1][C:2]1([CH3:11])[O:6][C@@:5]([CH3:10])([CH2:7][CH:8]=[O:9])[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11062680(S)-2,2,4-trimethyl-1,3-dioxolan-4-ethanolHCID 178526118HCID 178526118, compound

Product 1

HCID 53704870[(4S)-2,2,4-Trimethyl-1,3-dioxolan-4-yl]acetaldehydeYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.33 g of (S)-2,2,4-trimethyl-1,3-dioxolan-4-ethanol dissolved in 7 ml of absolute methylene chloride were added dropwise to a suspension of 7.59 g of pyridine chlorochromate in 30 ml of absolute methylene chloride. The reaction mixture was stirred at room temperature for 3 hours. By addition of 75 ml of ether, the chromium salt was precipitated and separated by filtration over 120 g of Kieselgel. After removal of the solvent on a rotary evaporator and distillation of the residue at 90°-100°/10 mmHg, there were obtained 3.00 g of (S)-2,2,4-trimethyl-1,3-dioxolan-4-acetaldehyde. [α]D20 =-35.5° (c=1.50; n-hexane).

Workup

  1. customthe chromium salt was precipitated
  2. customseparated by filtration over 120 g of Kieselgel
  3. customAfter removal of the solvent
  4. customon a rotary evaporator and distillation of the residue at 90°-100°/10 mmHg

Sources & evidence

ORD record
ord-12a8c9a631804af4a9c883b91cafc14d
Source dataset
uspto-grants-1980_11
Patent number
US04234490

Reaction notes

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