Sodium Hydroxide → 5,6-Bis(nitrooxy)hexan-1-ol

HRID 1361907Notes

Reaction equation

HRID 1361907 reaction equation
O1CCCC1.C(O)C.[N+](C1C=CC(C([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([O:29][N+:30]([O-:32])=[O:31])[CH2:24][O:25][N+:26]([O-:28])=[O:27])=O)=CC=1)([O-])=O.[OH-].[Na+]>C(=O)(O)[O-].[Na+]>[N+:26]([O-:28])([O:25][CH2:24][CH:23]([O:29][N+:30]([O-:32])=[O:31])[CH2:22][CH2:21][CH2:20][CH2:19][OH:18])=[O:27]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21873804Tetrahydrofuran ethanolHCID 765458355,6-Bis(nitrooxy)hexyl 4-nitrobenzoate

Product 1

HCID 579416215,6-Bis(nitrooxy)hexan-1-ol

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a tetrahydrofuran/ethanol 1:1 (12 mL) solution of 5,6-bis(nitrooxy)hexyl 4-nitrobenzoate (2.5 g, 6.70 mmol) at 0° C. was added 2.5 N sodium hydroxide (6.5 mL) dropwise. The solution was stirred at room temperature for 3 hours. The solution was diluted with a solution of sodium bicarbonate (10 mL) and extracted with ethyl acetate (3×25 mL). The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo, affording the title compound. 1H NMR (300 MHz, CDCl3) δ: 5.45-5.38 (m, 1H), 4.94 (dd, 1H), 4.73-4.67 (m, 1H), 4.43 (t, 1H), 3.40-3.36 (m, 2H), 1.75-1.68 (m, 2H), 1.43-1.36 (m, 4H).

Workup

  1. extractionextracted with ethyl acetate (3×25 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b59ccf9b6f544f6ab3c18fb11f911c9b
Source dataset
uspto-grants-2011_02
Patent number
US07880014B2

Reaction notes

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