Sulfuric Acid → 5-(4-Nitrophenyl)furfuryl alcohol

HRID 2052433

Reaction equation

HRID 2052433 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([CH:15]=[O:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+].[H][H].S(=O)(=O)(O)O>C(O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([CH2:15][OH:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 815675-(4-Nitrophenyl)-2-furaldehydeHCID 4311764Sodium borohydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 6882565-(4-Nitrophenyl)furfuryl alcohol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a heated suspension of 5-(4-nitrophenyl)-2-furancarboxaldehyde (176 g., 0.8 m.) and 1000 ml of ethanol was added a suspension of sodium borohydride (82 g.) in 1500 ml of ethanol. The solids dissolved and the solution turned very dark. The solution was stirred without external heating until hydrogen ceased to be evolved (22 hours). Upon stirring, the material solidified (pH 9-11). To the suspension was added a 5 percent sulfuric acid solution until the solution was just acidic (600 ml., pH 5-6). The dark mixture was dissolved upon heating at 60°-70° C. for 1 hour. After cooling, the solids were filtered and the filtrate was diluted with water to ppt. the product. The solids were extracted with boiling SDA-32 and the extracts were diluted with water. Total yield of 5-(p-nitrophenyl)-furfuryl alcohol was 150 grams (85%).

Workup

  1. additionwas added
  2. dissolutionThe solids dissolved
  3. custom(22 hours)
  4. stirringUpon stirring
  5. dissolutionThe dark mixture was dissolved
  6. temperatureupon heating at 60°-70° C. for 1 hour
  7. temperatureAfter cooling
  8. filtrationthe solids were filtered
  9. additionthe filtrate was diluted with water
  10. extractionThe solids were extracted with boiling SDA-32
  11. additionthe extracts were diluted with water

Sources & evidence

ORD record
ord-0d4ec5a3a9d94e2387a95fe01bc6122f
Source dataset
uspto-grants-1980_01
Patent number
US04185020

Linked notes

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