Neopentyl glycol → 2-((Benzyloxy)methyl)-5,5-dimethyl-1,3-dioxane

HRID 31565

Reaktionsgleichung

Reaktionsgleichung von HRID 31565
[CH2:1]([O:8][CH2:9][CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][C:13]([CH3:18])([CH2:16]O)[CH2:14][OH:15]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH:10]1[O:15][CH2:14][C:13]([CH3:18])([CH3:16])[CH2:12][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 31344Neopentyl glycolHCID 108989(Phenylmethoxy)acetaldehyde

Produkt 1

HCID 597925572-((Benzyloxy)methyl)-5,5-dimethyl-1,3-dioxaneAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of benzyloxyacetaldehyde (5 g, 33.3 mmol), 2,2-dimethyl-1,3-propanediol (4.16 g, 40 mmol) and toluene (70 ml), p-toluenesulfonic acid monohydrate (287 mg, 1.51 mmol) was added and refluxed for 4 hours while removing water by the Dean-Stark apparatus. After the reaction mixture was cooled to room temperature, triethylamine (4 ml) was added to the reaction mixture and the solvent was removed by evaporation. The residue was purified by silica gel column chromatography (silica gel: 200 g, elution solvent: ethyl acetate/heptane=1/9) to obtain the title compound (7.6 g, yield: 96.6%) as a colorless oil.

Aufarbeitung

  1. additionwas added
  2. temperaturerefluxed for 4 hours
  3. customwhile removing water by the Dean-Stark apparatus
  4. additiontriethylamine (4 ml) was added to the reaction mixture
  5. customthe solvent was removed by evaporation
  6. customThe residue was purified by silica gel column chromatography (silica gel: 200 g, elution solvent: ethyl acetate/heptane=1/9)

Quellen und Nachweise

ORD-Eintrag
ord-95876f928d594ffb87130057875b8aae
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425634B2

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