Hydrochloric Acid → 4-Hydroxy-4'-octylazobenzene

HRID 1111265ノート

反応式

HRID 1111265 の反応式
[CH2:1]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl.[N:17]([O-])=O.[Na+].[OH-].[Na+].[C:23]1([OH:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[OH:29][C:23]1[CH:28]=[CH:27][C:26]([N:17]=[N:13][C:12]2[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:15][CH:14]=2)=[CH:25][CH:24]=1

参加物

7

反応物 5

HCID 313Hydrochloric Acid2 回HCID 996PhenolHCID 14798Sodium HydroxideHCID 853464-OctylanilineHCID 23668193Sodium Nitrite

生成物 1

HCID 27534414-Hydroxy-4'-octylazobenzene収率 59%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

35 g (0.17M) of 4-octylaniline was cooled below 0° C. and 85 g of 10% aqueous hydrochloric acid solution was added thereto. To the mixture was then added dropwise an aqueous solution of 12.0 g of sodium nitrite in 68 ml of water while cooling the mixture so as not to exceed 0° C. After the dropwise addition, the reaction was continued for 30 minutes. The reaction mixture was transferred into a dropping funnel and added dropwise therefrom into 170 g of an 8%-NaOH aqueous solution containing 16 g of phenol while the temperature was kept below 5° C. After the dropwise addition, stirring was continued for 1 hour, and thereafter a 10% aqueous hydrochloric acid solution was added until the pH reached 5-6 thereby precipitating the reaction product. The precipitate was separated by filtration, washed with water and dried under reduced pressure overnight. The dried product was washed with 500 ml of petroleum ether and dried under reduced pressure to obtain 30.8 g (0.10M) of 4-hydroxy-4'-octylazobenzene. The yield was 59%.

後処理

  1. temperaturewhile cooling the mixture so as not
  2. customto exceed 0° C
  3. additionAfter the dropwise addition
  4. customThe reaction mixture was transferred into a dropping funnel
  5. additionadded dropwise
  6. customwas kept below 5° C
  7. additionAfter the dropwise addition
  8. waitwas continued for 1 hour
  9. customthereby precipitating the reaction product
  10. customThe precipitate was separated by filtration
  11. washwashed with water
  12. customdried under reduced pressure overnight
  13. washThe dried product was washed with 500 ml of petroleum ether
  14. customdried under reduced pressure

出典と根拠

ORDレコード
ord-e157f5b090334f68b965a4be808ffd5e
出典データセット
uspto-grants-1990_12
特許番号
US04979805

反応ノート

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