Furfural → HCID 20100035, compound

HRID 268087Notes

Reaction equation

HRID 268087 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:16]=[CH:15][C:13](N)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N([O-])=O.[Na+].[CH:21](=[O:27])[C:22]1[O:26][CH:25]=[CH:24][CH:23]=1>O.Cl>[CH2:2]([O:9][C:10]1[CH:16]=[CH:15][C:13]([C:25]2[O:26][C:22]([CH:21]=[O:27])=[CH:23][CH:24]=2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7362FurfuralHCID 27238314-Benzyloxyaniline hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 20100035HCID 20100035, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

A mixture of 236 g (1.0 mole) of p-benzyloxyaniline hydrochloride in 1.5 l of water and 230 ml of conc. HCl was warmed on a steam bath for 11/2 hours. No solution was effected. The mixture was then cooled down to 0°-5° and a solution of 76 g (1.1 mole) of sodium nitrite in 500 ml of water was added in about 1 hour while keeping the temperature at 4°-7°. The mixture was allowed to stir further for an additional 45 minutes while the temperature gradually rose to 10°. Furfural (192 g, 2 moles) and 55 g of cupric chloride dihydrate in a minimum amount of water was added and the mixture was allowed to stir at ambient temperature overnight. Solid started to separate after 2 days of stirring. The solid was collected, washed well with water. The filtrate and the water washings were combined and allowed to stir for an additional 4 days while more solid separated. The dark gummy solids were combined, triturated with ether, filtered and air dried. Repeated recrystallizations from hot cyclohexane gave 48.5 g (17.5%).

Workup

  1. temperaturewas warmed on a steam bath for 11/2 hours
  2. temperatureThe mixture was then cooled down to 0°-5°
  3. customat 4°-7°
  4. customgradually rose to 10°
  5. stirringto stir at ambient temperature overnight
  6. customto separate after 2 days
  7. stirringof stirring
  8. customThe solid was collected
  9. washwashed well with water
  10. stirringto stir for an additional 4 days while more solid
  11. customseparated
  12. customtriturated with ether
  13. filtrationfiltered
  14. customair dried
  15. customrecrystallizations from hot cyclohexane
  16. customgave 48.5 g (17.5%)

Sources & evidence

ORD record
ord-3dae6e50c8ac48fb92947d1b0c910a19
Source dataset
uspto-grants-1976_03
Patent number
US03946049

Reaction notes

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