Acetic Acid → 1-Nitroadamantane

HRID 992149

Reaction equation

HRID 992149 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH:11][N:12]1C(=O)C2=CC=CC=C2C1=O.C(O)(=[O:25])C>>[N+:12]([C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2)([O-:11])=[O:25]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 9238Adamantane2×HCID 10665N-Hydroxyphthalimide

Product 1

HCID 641651-NitroadamantaneYield 64%

Procedure

Into a flask, 1 mmole of adamantane, 0.1 mmole of N-hydroxyphthalimide and 6 ml of acetic acid were added to mix. The flask was purged by nitrogen monoxide NO (about 1L) and oxygen O2 (about 1L), and then the mixture was reacted for 20 hours at 110° C. with stirring. The reaction products were analyzed by gas chromatography, and, as a result, the conversion of adamantane was 90%, and 1-nitroadamantane (yield 64%) and 1,3-dinitroadamantane (yield 12%) were formed.

Workup

  1. additionto mix
  2. customThe flask was purged by nitrogen monoxide NO (about 1L) and oxygen O2 (about 1L)
  3. customthe mixture was reacted for 20 hours at 110° C.

Sources & evidence

ORD record
ord-aec03bee9da5464ca1e458d8bae2b610
Source dataset
uspto-grants-2002_10
Patent number
US06468487B1

Linked notes

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