Benzaldehyde → L-Gulose

HRID 345263Notes

Reaction equation

HRID 345263 reaction equation
C(N(C1C=CC=CC=1)N=[CH:10][C@H:11]([C@H:13]([C@@H:15]([C@H:17]([CH2:19][OH:20])[OH:18])[OH:16])[OH:14])[OH:12])C1C=CC=CC=1.O.C(=[O:35])C1C=CC=CC=1.C(O)(=O)C1C=CC=CC=1>C(O)C>[O:20]=[CH:19][C@H:17]([C@H:15]([C@@H:13]([C@H:11]([CH2:10][OH:35])[OH:12])[OH:14])[OH:16])[OH:18]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 243Benzoic AcidHCID 962WaterHCID 67932689L-gulose benzylphenylhydrazone

Product 1

HCID 80127L-Gulose

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The L-gulose benzylphenylhydrazone was refluxed for three hours with 100 ml. of water and 20 ml. of ethanol containing 7.5 ml. of benzaldehyde and 0.8 grams of benzoic acid. After cooling, the solution was decanted from the crystals of benzaldehyde benzylphenylhydrazone and extracted several times with ether to remove the benzaldehyde and benzoic acid. The solution was then decolorized with activated carbon and concentrated under reduced pressure to a colorless syrup to yield 3.4 grams of syrupy L-gulose.

Workup

  1. temperatureAfter cooling
  2. customthe solution was decanted from the crystals of benzaldehyde benzylphenylhydrazone
  3. extractionextracted several times with ether
  4. customto remove the benzaldehyde and benzoic acid
  5. concentrationconcentrated under reduced pressure to a colorless syrup

Sources & evidence

ORD record
ord-4e48fc8e4a234686a9bf04b152a20c5e
Source dataset
uspto-grants-1991_10
Patent number
USRE033719

Reaction notes

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