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Water → (4S)-2,2-Dimethyl-4-(4-cyanophenoxy)methyl-1,3-dioxolane

HRID 466220
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 466220
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[OH-:10].[K+].[OH2:12]>CO>[CH3:3][C:2]1([CH3:9])[O:12][C@@H:5]([CH2:6][O:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:4][O:10]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 130194-CyanophenolHCID 14797Potassium Hydroxide

Produkt 1

HCID 15066863(4S)-2,2-Dimethyl-4-(4-cyanophenoxy)methyl-1,3-dioxolane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A solution of 4-hydroxy benzonitrile (55 g) in methanol (100 ml) was treated with potassium hydroxide (29 g) in water (30 ml) and evaporated at reduced pressure. The remaining potassium salt was dissolved in dry dimethylformamide (75 ml) and (4R)-2,2-dimethyl-4 - methanesulfonyloxymethyl-1,3-dioxolane, 82.2 g, was add stirring at 110° C. for 20 h, allowed to cool and distributed between ether and water. The aqueous phase was extracted three times with ether, the combined ether phases washed three times with 10% aqueous potassium hydroxide and twice with water, dried over anhydrous sodium sulfate and evaporated. Yield 77 g of the title compound.

Aufarbeitung

  1. customevaporated at reduced pressure
  2. dissolutionThe remaining potassium salt was dissolved in dry dimethylformamide (75 ml)
  3. addition(4R)-2,2-dimethyl-4 - methanesulfonyloxymethyl-1,3-dioxolane, 82.2 g, was add
  4. temperatureto cool
  5. extractionThe aqueous phase was extracted three times with ether
  6. washthe combined ether phases washed three times with 10% aqueous potassium hydroxide
  7. dry with materialtwice with water, dried over anhydrous sodium sulfate
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-104d16223d4a4b9ca9b898b2d5970fa2
Quelldatensatz
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05155133

Notizen zur Reaktion

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