Sodium Cyanide → 4-(4Acetyl-3-hydroxy-2-propylphenoxy)butane nitrile

HRID 622231노트

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HRID 622231 반응식
[C:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12]Br)=[C:6]([CH2:16][CH2:17][CH3:18])[C:5]=1[OH:19])(=[O:3])[CH3:2].[C-]#[N:21].[Na+]>CN(C)C=O>[C:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]#[N:21])=[C:6]([CH2:16][CH2:17][CH3:18])[C:5]=1[OH:19])(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 8929Sodium CyanideHCID 133716024-(4-Acetyl-3-hydroxy-2-propylphenoxy)butyl bromide

생성물 1

HCID 137633064-(4Acetyl-3-hydroxy-2-propylphenoxy)butane nitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 30.0 g. (91.1 mmoles) of 4-(4-acetyl-3-hydroxy-2-propylphenoxy)butyl bromide and 4.91 g. (100.2 mmoles) of sodium cyanide in 225 ml. of dimethylformamide was heated to 75°-85° C. for about 17 hours. The reaction mixture was cooled to room temperature, filtered, and evaporated in vacuo at 75° C. Cold 0.1N hydrochloric acid was added to the residue, and the residue was extracted into ethyl acetate. The ethyl acetate layer was twice washed with 0.1N hydrochloric acid, dried over sodium sulfate, and evaporated in vacuo to yield 21.02 g. of 4-(4-acetyl-3-hydroxy-2-propylphenoxy)butane nitrile as a dark amber oil which crystallized as it cooled.

후처리

  1. filtrationfiltered
  2. customevaporated in vacuo at 75° C
  3. additionCold 0.1N hydrochloric acid was added to the residue
  4. extractionthe residue was extracted into ethyl acetate
  5. washThe ethyl acetate layer was twice washed with 0.1N hydrochloric acid
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customto yield 21.02 g
  9. customof 4-(4-acetyl-3-hydroxy-2-propylphenoxy)butane nitrile as a dark amber oil which crystallized as it
  10. temperaturecooled

출처 및 근거

ORD 기록
ord-a47fb6b4382549eca90c253bad18fb44
출처 데이터셋
uspto-grants-1988_09
특허 번호
US04769482

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