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

HRID 1980085

반응식

HRID 1980085 반응식
[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]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 5975CyanideHCID 69112,6-Di-tert-butyl-4-(methoxymethyl)phenol2회HCID 8929Sodium Cyanide

생성물 1

HCID 615568(3,5-Di-tert-butyl-4-hydroxyphenyl)acetonitrile수율 95.7%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9ef2697abd314a7c9b03ce16e1c63e41
출처 데이터셋
uspto-grants-1984_11
특허 번호
US04485051

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