Sodium Hydroxide → 4,5-Bis(nitrooxy)pentyl alcohol

HRID 1437606Notes

Reaction equation

HRID 1437606 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH:8]([O:14][N+:15]([O-:17])=[O:16])[CH2:9][O:10][N+:11]([O-:13])=[O:12])(=O)C.[OH-].[Na+]>CCO>[N+:15]([O:14][CH:8]([CH2:9][O:10][N+:11]([O-:13])=[O:12])[CH2:7][CH2:6][CH2:5][OH:4])([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 574568054,5-Bis(nitrooxy)pentyl acetate

Product 1

HCID 579416234,5-Bis(nitrooxy)pentyl alcoholYield 40.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 18.7 g of 4,5-bis(nitrooxy)pentyl acetate in 150 mL of EtOH at 25° C. was added 2.96 g of NaOH. The mixture was stirred for 90 min, quenched by addition of NaHCO3 sat., extracted with EtOAc, washed with brine and dried over sodium sulfate. Purification by flash chromatography afforded 6.3 g of the desired compound as an orange oil. 1H NMR (acetone-d6, 500 MHz): δ 5.56 (m, 1H), 5.01 (dd, 1H), 4.73 (dd, 1H), 3.68 (t, 1H), 3.60 (m, 2H), 1.93-1.86 (m, 2H), 1.69-1.64 (m, 2H).

Workup

  1. customquenched by addition of NaHCO3 sat.
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customPurification by flash chromatography

Sources & evidence

ORD record
ord-b0759221811344dca28b519b88fc798d
Source dataset
uspto-grants-2009_11
Patent number
US07622502B2

Reaction notes

Loading…