Water → 5,5'-[Methylenebis(oxy)]bis(4,4-dinitropentan-1-ol)

HRID 255390Notes

Reaction equation

HRID 255390 reaction equation
[N+:1]([C:4]([N+:29]([O-:31])=[O:30])([CH2:11][O:12][CH2:13][O:14][CH2:15][C:16]([N+:26]([O-:28])=[O:27])([N+:23]([O-:25])=[O:24])[CH2:17][CH2:18][C:19](OC)=[O:20])[CH2:5][CH2:6][C:7](OC)=[O:8])([O-:3])=[O:2].O>B.C1COCC1>[N+:1]([C:4]([N+:29]([O-:31])=[O:30])([CH2:11][O:12][CH2:13][O:14][CH2:15][C:16]([N+:23]([O-:25])=[O:24])([N+:26]([O-:28])=[O:27])[CH2:17][CH2:18][CH2:19][OH:20])[CH2:5][CH2:6][CH2:7][OH:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 962Water2×HCID 20165452HCID 20165452, compound

Product 1

HCID 230483335,5'-[Methylenebis(oxy)]bis(4,4-dinitropentan-1-ol)

Reagents, catalysts & solvents 1

HCID 2723981Borane;tetrahydrofuranSolvent

Procedure

Dimethyl 4,4,10,10-tetranitro-6,8-dioxatridecane-1,13-dioate (28.8 g) was dissolved in 139 mL of BH3.THF with ice-cooling and under a nitrogen atmosphere. The solution was stirred at room temperature for 3 days, after which time 27 mL of water was added slowly and the mixture was heated at 60° C. for 5 minutes. After cooling, the mixture was poured into 200 mL of water, and the product was extracted with ether. The ether solution was washed with aqueous sodium bicarbonate solution, then with water, and dried (MgSO4) After removal of the solvent, the crude product was recrystallized from dichloromethane. Yield: 19.9 g (79%); M.P. 72.5°-3.5° C. 1H NMR spectrum (CDCl3 /TMS): δ 4.76 (s, 2H); 4.41 (s, 4H); 2.69 (m, 4H); 1.59 (m. 4H).

Workup

  1. temperaturecooling and under a nitrogen atmosphere
  2. temperaturethe mixture was heated at 60° C. for 5 minutes
  3. temperatureAfter cooling
  4. extractionthe product was extracted with ether
  5. washThe ether solution was washed with aqueous sodium bicarbonate solution
  6. dry with materialwith water, and dried (MgSO4)
  7. customAfter removal of the solvent
  8. customthe crude product was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-43b4e8df805249e79b05612a754afddb
Source dataset
uspto-grants-1987_10
Patent number
USH0000351

Reaction notes

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