Sulfuric Acid → L-mannose phenylhydrazone

HRID 1706582Notes

Reaction equation

HRID 1706582 reaction equation
[N+:1]([CH2:4][C@@H:5]([C@@H:7]([C@H:9]([C@H:11]([CH2:13][OH:14])[OH:12])[OH:10])[OH:8])[OH:6])([O-])=O.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+].[C:25]1([NH:31]N)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>[OH-].[Na+].O.C(O)(=O)C>[C:25]1([NH:31][N:1]=[CH:4][C@@H:5]([C@@H:7]([C@H:9]([C@H:11]([CH2:13][OH:14])[OH:12])[OH:10])[OH:8])[OH:6])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 7516PhenylhydrazineHCID 1111301-Deoxy-1-nitro-L-mannitolHCID 516892Sodium Bicarbonate

Product 1

HCID 86737045L-mannose phenylhydrazone

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

1-Deoxy-1-nitro-L-mannitol (20 g.) was dissolved in 2 N sodium hydroxide (60 ml.), and the solution was immediately added dropwise to a stirred solution of sulfuric acid (30 ml.) in water (36 ml.) at room temperature. Some cooling (ice bath) was used to keep the reaction mixture at 22°±5°. The solution was then diluted to 400 ml. with water, just neutralized with solid sodium hydrogen carbonate, and a solution of phenylhydrazine (12 ml.) in glacial acetic acid (28 ml.) added. The mixture was stirred overnight at 5° and then filtered, and the L-mannose phenylhydrazone was washed with cold water, ethanol, and ether. Recrystallization from ethanol gave pure L-mannose phenylhydrazone, m.p. 198°-199°, [α]D -33.5° (c 2.5, pyridine) compared with m.p. 199°-200°, [α]D +34° for the D-isomer, p. 240).

Workup

  1. customat 22°±5°
  2. additionThe solution was then diluted to 400 ml
  3. filtrationfiltered
  4. washthe L-mannose phenylhydrazone was washed with cold water, ethanol, and ether
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-99d73ef9a1a349e79fe8e97b5ce58c5a
Source dataset
uspto-grants-1980_06
Patent number
US04207413

Reaction notes

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