Hydrochloric Acid → Benzenediazonium, 4-methoxy-, hexafluorophosphate(1-)

HRID 1974009Notes

Reaction equation

HRID 1974009 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.[N:11]([O-])=O.[Na+].[F:15][P-:16]([F:21])([F:20])([F:19])([F:18])[F:17].[NH4+]>O>[F:15][P-:16]([F:21])([F:20])([F:19])([F:18])[F:17].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]#[N:11])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7732P-AnisidineHCID 9793912Ammonium hexafluorophosphateHCID 23668193Sodium Nitrite

Product 1

HCID 101827Benzenediazonium, 4-methoxy-, hexafluorophosphate(1-)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
-5 °C

Procedure

1440 cc. of 5N aqueous hydrochloric acid was charged into a 3000 cc. capacity vessel equipped with a stirrer, thermometer, condenser and addition funnel. 184.5 g. (1.5M) of p-anisidine was added and the mixture stirred at room temperature until complete conversion to the ammonium salt was achieved. The solution was cooled in an ice-methanol bath to -5° C. Diazotization was achieved by adding 184.5 g. (1.52M) of sodium nitrite in 300 ml of water dropwise over a 30-minute period while maintaining the temperature between 0°-5° C. A solution of 244.5 g. (1.5M) of ammonium hexafluorophosphate in 300 ml of water was added to precipitate the hexafluorophosphate salt. The salt was filtered, washed chloride-free and vacuum-dried at 25° C.

Workup

  1. customcapacity vessel equipped with a stirrer
  2. additionthermometer, condenser and addition funnel
  3. additionby adding 184.5 g
  4. customto precipitate the hexafluorophosphate salt
  5. filtrationThe salt was filtered
  6. washwashed chloride-free
  7. customvacuum-dried at 25° C.

Sources & evidence

ORD record
ord-3626ee4b85cc4a4da991fb0b6b13b394
Source dataset
uspto-grants-1976_12
Patent number
US04000115

Reaction notes

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