Formaldehyde → 2-Hydroxymethyl-2-phenylheptanenitrile

HRID 540382Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 540382
[C:1]1([CH:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:17]=[O:18]>CN(C=O)C>[OH:18][CH2:17][C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:8]#[N:9]

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 24758Sodium hydrideHCID 126520202-Phenylheptanenitrile

Produkt 1

HCID 669878522-Hydroxymethyl-2-phenylheptanenitrileAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5.14 g (27.4 mmol) of 2-phenylheptanenitrile are added to a suspension of 1.34 g of 60% NaH in 50 ml of DMF cooled to 0° C. After stirring for 30 minutes, 7.6 g (220 mmol) of paraformaldehyde are added portionwise. The reaction medium is left to stir at ambient temperature for 6 hours and then hydrolysed with ice and extracted with diethyl ether. The organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over sodium sulphate, filtered and evaporated under pressure. The crude product obtained is purified by silica gel chromatography (eluent 8/2 heptane/ethyl acetate). 4.24 g in the form of a pale yellow oil are obtained with a yield of 71%.

Aufarbeitung

  1. waitThe reaction medium is left
  2. stirringto stir at ambient temperature for 6 hours
  3. extractionhydrolysed with ice and extracted with diethyl ether
  4. washThe organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated under pressure

Quellen und Nachweise

ORD-Eintrag
ord-16b9849e45e9416fa2bfd3498008499e
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871187B2

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