Hydrochloric Acid → 4-Hydroxy-4'-octylazobenzene

HRID 1111265

Reaction equation

HRID 1111265 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

HCID 27534414-Hydroxy-4'-octylazobenzeneYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-e157f5b090334f68b965a4be808ffd5e
Source dataset
uspto-grants-1990_12
Patent number
US04979805

Linked notes

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