Hydrochloric Acid → HCID 14316717, compound

HRID 274106Notes

Reaction equation

HRID 274106 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.Cl.N([O-])=O.[Na+].[O:14]1[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15]1>O.CC(C)=O>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]2[O:14][CH:18]=[CH:17][C:16]=2[C:19]([OH:21])=[O:20])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7813p-ToluidineHCID 102683-Furoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 14316717HCID 14316717, compoundYield 15.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent4×

Conditions

Temperature
0 °C

Procedure

70.7 g of p-toluidine, cooled with a bath of water and ice, are treated with 205 ml of 36% HCl. The mixture is then stirred at 55°-60° C. for 30 min before being cooled to 0° C. again. A solution of 45 g of NaNO2 in 220 ml of water is then introduced. The mixture is stirred for 1 h at 0° C. This cold solution is introduced into a mixture of 49.3 g of 3-furanoic acid, 220 ml of acetone, 23.4 g of CuCl2 and 6.3 g of water, cooled to -5° C. The whole is stirred at 0° C. for 2 h and then at room temperature for 48 h. It is extracted twice with ether and the organic phase is decanted, dried and concentrated to give an oil, which gives crystals when treated with water. The crystals are filtered off and washed with 50 ml of a 50% methanol/water mixture to give 13.4 g of 2-(4-methylphenyl)-3-furanoic acid.

Workup

  1. stirringThe mixture is stirred for 1 h at 0° C
  2. temperaturecooled to -5° C
  3. stirringThe whole is stirred at 0° C. for 2 h
  4. waitat room temperature for 48 h
  5. extractionIt is extracted twice with ether
  6. customthe organic phase is decanted
  7. customdried
  8. concentrationconcentrated
  9. customto give an oil, which
  10. customgives crystals when
  11. filtrationThe crystals are filtered off
  12. washwashed with 50 ml of a 50% methanol/water mixture

Sources & evidence

ORD record
ord-cba1164fe76c41acaf6b5528da40c795
Source dataset
uspto-grants-1995_02
Patent number
US05387747

Reaction notes

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