Butyl bromide → 4-Butoxy-2,6-dimethylazobenzene

HRID 1856289노트

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HRID 1856289 반응식
[Na].[CH3:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[C:5]([CH3:10])[C:4]=1[N:11]=[N:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Br[CH2:20][CH2:21][CH2:22][CH3:23]>C(O)C>[CH2:20]([O:9][C:7]1[CH:6]=[C:5]([CH3:10])[C:4]([N:11]=[N:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:3]([CH3:2])[CH:8]=1)[CH2:21][CH2:22][CH3:23]

참가 물질

5

반응물 3

HCID 8002Butyl bromideHCID 33198223,5-Dimethyl-4-(phenyldiazenyl)phenolHCID 5360545Sodium

생성물 1

HCID 537623114-Butoxy-2,6-dimethylazobenzene

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of sodium (2.0 g, 0.09 mole) in absolute ethanol (119 ml) was added 2,6-dimethyl-4-hydroxyazobenzene (18.3 g, 0.08 mole) prepared according to B. C. Saunders and G. H. R. Watson, Biochem. J. 46:629-233 (1950). To the resulting orange-red solution was added 1-bromobutane (22.3 g, 0.162 mole) slowly from a separatory funnel and the mixture was refluxed for five hours. When cool, the precipitated sodium bromide was filtered off and the filtrate was evaporated to dryness. The residue was taken up in ether and the ether solution was extracted, first with 0.5 M sodium hydroxide and then once with water. The ether phase was dried (Na2SO4), filtered, and evaporated to dryness. The yield was over 90%. This material is satisfactory for the next step. After recrystallization from 95% ethanol, it melted at 47°-47.5° C. Calcd. for C18H22N2O: C 76.6, H 7.85, N 9.92. Found: C 76.7, H 7.84, N 9.86.

후처리

  1. customprepared
  2. temperaturethe mixture was refluxed for five hours
  3. temperatureWhen cool
  4. filtrationthe precipitated sodium bromide was filtered off
  5. customthe filtrate was evaporated to dryness
  6. extractionthe ether solution was extracted, first with 0.5 M sodium hydroxide
  7. dry with materialThe ether phase was dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customAfter recrystallization from 95% ethanol, it melted at 47°-47.5° C

출처 및 근거

ORD 기록
ord-a494e2008c0f4d6d947baf46639296ba
출처 데이터셋
uspto-grants-1980_08
특허 번호
US04218477

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