Nitric Acid → tetrahydro-2H-pyran-3-ol nitrate

HRID 1995471Notes

Reaction equation

HRID 1995471 reaction equation
[N+:1]([O-:4])([OH:3])=[O:2].[O:5]1[CH2:10][CH2:9][CH2:8][CH:7](O)[CH2:6]1>C(OC(=O)C)(=O)C>[N+:1]([O:4][CH:7]1[CH2:8][CH2:9][CH2:10][O:5][CH2:6]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 12256033tetrahydro-2H-pyran-3-ol

Product 1

HCID 13224378tetrahydro-2H-pyran-3-ol nitrate

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

In a reaction vessel was placed 50 ml acetic anhydride. While cooling, 14 ml of 90 percent fuming nitric acid was added. Following this, 25 g of tetrahydro-2H-pyran-3-ol was added dropwise at -8° to -10° C. over a one hour period. Stirring was continued for 1.5 hours at -10° C. The mixture was then allowed to warm to room temperature and then poured into an ice-water mixture. The organic phase settled and was separated. The organic phase was diluted with methylene chloride and also washed with aqueous NaHCO3 and dried over MgSO4. The solvent was removed under vacuum leaving 24.04 g of tetrahydro-2H-pyran-3-ol nitrate. The structure was confirmed by IR and NMR analysis.

Workup

  1. customIn a reaction vessel was placed
  2. temperatureWhile cooling
  3. additionwas added dropwise at -8° to -10° C. over a one hour period
  4. customwas separated
  5. additionThe organic phase was diluted with methylene chloride
  6. washalso washed with aqueous NaHCO3
  7. dry with materialdried over MgSO4
  8. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-98cd71fc582d42829c733a3fb4a2c434
Source dataset
uspto-grants-1983_09
Patent number
US04405333

Reaction notes

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