Hydrochloric Acid → (3,5-Di-tert-butyl-4-hydroxyphenyl)acetonitrile

HRID 1980085

Reaktionsgleichung

Reaktionsgleichung von HRID 1980085
[C-:1]#[N:2].[Na+].[C-]#N.CO[CH2:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:12]([OH:19])=[C:11]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:10]=1.Cl>CO.C1(C)C=CC=CC=1>[OH:19][C:12]1[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:14][C:9]([CH2:8][C:1]#[N:2])=[CH:10][C:11]=1[C:20]([CH3:23])([CH3:22])[CH3:21]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 5975CyanideHCID 69112,6-Di-tert-butyl-4-(methoxymethyl)phenol2×HCID 8929Sodium Cyanide

Produkt 1

HCID 615568(3,5-Di-tert-butyl-4-hydroxyphenyl)acetonitrileAusbeute 95,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Sodium cyanide (2.94 g; 50 mmol) was slurried in methanol (20 mLs) in a 100 mL round bottom flask and the slurry was heated to a gentle reflux. To the cyanide slurry, a solution of 4-methoxymethyl-2,6-di-t-butyl phenol (12.5 g; 50 mmol), toluene (20 mLs) and methanol (25 mLs) was added dropwise over a period of time of 55 minutes. The resultant black reaction mixture was refluxed an additional 35 minutes after complete addition of the 4-methoxymethyl-2,6-di-t-butyl phenol. Upon cooling to ambient temperature, 2N hydrochloric acid (40 mLs) was added to the reaction flask. A yellow slurry which resulted was extracted with diethyl ether. The ether extract was dried (MgSO4) and concentrated in vacuo to afford 11.74 grams of 4-hydroxy-3,5-di-t-butylphenylacetonitrile as identified by NMR. Analysis by VPC indicated a 95% yield of 4-hydroxy-2,6-di-t-butylphenylacetonitrile.

Aufarbeitung

  1. temperaturethe slurry was heated to a gentle reflux
  2. customThe resultant black reaction mixture
  3. temperaturewas refluxed an additional 35 minutes
  4. customA yellow slurry which resulted
  5. extractionwas extracted with diethyl ether
  6. extractionThe ether extract
  7. dry with materialwas dried (MgSO4)
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9ef2697abd314a7c9b03ce16e1c63e41
Quelldatensatz
uspto-grants-1984_11
Patentnummer
US04485051

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