Hydrochloric Acid → 33228-49-8

HRID 867353Notes

Reaction equation

HRID 867353 reaction equation
[CH2:1]([C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Cl.[N:15]([O-])=O.[Na+].[OH-].[Na+].[C:21]1([OH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O>[OH:27][C:21]1[CH:26]=[CH:25][C:24]([N:15]=[N:11][C:10]2[CH:9]=[CH:8][C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:13][CH:12]=2)=[CH:23][CH:22]=1

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 996PhenolHCID 14798Sodium HydroxideHCID 363824-HexylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 13570282833228-49-8Yield 120.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30.1 g (0.17 M) of 4-hexylaniline was cooled to 0° C. or below, 85 gof 10% aqueous hydrochloric acid solution was added, and then a solution of11.6 g of sodium nitrite in 68 g of water was added. During the addition, the mixture was cooled so as not to exceed 0° C. After the addition, the mixture was allowed to react for 30 minutes, transferred into a dropping funnel and added dropwise into 170 g of an 8% NaOH aqueoussolution containing 16 g of phenol held at 5° C. or below. After theaddition, the mixture was stirred for 0.5 hour, and then 10% hydrochloric acid aqueous solution was added thereto until a pH of 5-6 to precipitate the reaction product. The precipitate was separated by filtration, washed with water and dried overnight under reduced pressure. After the drying, the product was washed with 500 ml of petroleum ether and further dried under reduced pressure to obtain 29.6 g (0.10M) of 4-hydroxy-4'-hexylazobenzene. The yield was 59%.

Workup

  1. additionDuring the addition
  2. temperaturethe mixture was cooled so as not
  3. customto exceed 0° C
  4. additionAfter the addition
  5. customto react for 30 minutes
  6. customtransferred into a dropping funnel
  7. customheld at 5° C. or below
  8. customuntil a pH of 5-6 to precipitate the reaction product
  9. customThe precipitate was separated by filtration
  10. washwashed with water
  11. customdried overnight under reduced pressure
  12. washAfter the drying, the product was washed with 500 ml of petroleum ether
  13. customfurther dried under reduced pressure

Sources & evidence

ORD record
ord-e136669893644a538cc9a539a116c1bd
Source dataset
uspto-grants-1988_10
Patent number
US04775223

Reaction notes

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