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

HRID 1856289ノート

反応式

HRID 1856289 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 537623114-Butoxy-2,6-dimethylazobenzene

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a494e2008c0f4d6d947baf46639296ba
出典データセット
uspto-grants-1980_08
特許番号
US04218477

反応ノート

読み込み中…