Hydrochloric Acid → HCID 135702827, compound

HRID 1111263Notes

Reaction equation

HRID 1111263 reaction equation
[CH2:1]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Cl.[N:16]([O-])=O.[Na+].[OH-].[Na+].[C:22]1([OH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O>[OH:28][C:22]1[CH:27]=[CH:26][C:25]([N:16]=[N:12][C:11]2[CH:10]=[CH:9][C:8]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:14][CH:13]=2)=[CH:24][CH:23]=1

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 996PhenolHCID 14798Sodium HydroxideHCID 142169p-HeptylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 135702827HCID 135702827, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

32.9 g (0.17M) of 4-heptylaniline 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 12.1 g of sodium nitrite in 70 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 300 ml 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 to 6 thereby precipitating the reaction product. The precipitate was placed on a filter, 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 34.7 g (0.12M) of 4-hydroxy-4'-heptylazobenzene. The yield was 70%.

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. washwashed with water
  11. customdried under reduced pressure overnight
  12. washThe dried product was washed with 500 ml of petroleum ether
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-21240461abe34a3db35359fa0b67b83e
Source dataset
uspto-grants-1990_12
Patent number
US04979805

Reaction notes

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