4-Nitrophenol → HCID 13298512, compound

HRID 2352008Notes

Reaction equation

HRID 2352008 reaction equation
C(O[C@@H:5]1[O:22][C@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)C.[CH:28]1[C:33]([N+:34]([O-:36])=[O:35])=[CH:32][CH:31]=[C:30]([OH:37])[CH:29]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[C:8]([O:7][C@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:22][C@H:5]1[O:37][C:30]1[CH:31]=[CH:32][C:33]([N+:34]([O-:36])=[O:35])=[CH:28][CH:29]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 2

HCID 9804-NitrophenolHCID 12236021HCID 12236021, compound

Product 1

HCID 13298512HCID 13298512, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 11192Zinc AcetateCatalystHCID 1140TolueneSolvent

Procedure

A 19.5 g (0.05 mole) quantity of penta-O-acetyl-β-D-mannopyranose and 13.9 g (0.10 mole) of p-nitrophenol were heated at 130° C. under reduced pressure of 20 mmHg. To the melt obtained were added 0.25 g of 12-molybdophosphoric acid and 0.05 g of zinc acetate and the mixture was reacted under reduced pressure for 30 minutes. The reaction mixture was dissolved in 100 ml of toluene and the solution was washed with 6 portions of 50 ml of 1.0M-NaoH aqueous solution and with 2 portions of 50 ml of water. After the toluene layer was evaporated to dryness under reduced pressure, the semisolid obtained was purified by silica gel column chromatography using toluene-acetone (20 : 1, v/v) as an eluent, giving 12.2 g of p-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside in a yield of 52.0%. M.p. 142° to 143° C.

Workup

  1. customTo the melt obtained
  2. customthe mixture was reacted under reduced pressure for 30 minutes
  3. washthe solution was washed with 6 portions of 50 ml of 1.0M-NaoH aqueous solution and with 2 portions of 50 ml of water
  4. customAfter the toluene layer was evaporated to dryness under reduced pressure
  5. customthe semisolid obtained
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-aa66a47706f8416db3ca2efe8750b3a0
Source dataset
uspto-grants-1989_10
Patent number
US04874852

Reaction notes

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