D-Glucose → Nitrous acid, hexyl ester

HRID 1579000Notes

Reaction equation

HRID 1579000 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[N:8]([O-:10])=[O:9].CN([S+](N(C)C)N(C)C)C.OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O.[N+](CCCCCC)([O-])=O>C(#N)C>[N:8]([O:10][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:9]

Participants

6

Reactant 4

HCID 5793D-GlucoseHCID 81011-BromohexaneHCID 125891-NitrohexaneHCID 21557485Tris(dimethylamino)sulfonium nitrite

Product 1

HCID 6365123Nitrous acid, hexyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 165-mg (1 mmole) sample of 1-bromohexane was added to 0.5 ml (1 mmole) of 2M tris(dimethylamino)sulfonium nitrite in acetonitrile. The course of the reaction was followed by glc analysis. No further reaction occurred after 15 min. Glc analysis showed that 1-nitrohexane and 1-hexyl nitrite were formed in a 70:30 ratio.

Workup

  1. customNo further reaction

Sources & evidence

ORD record
ord-b299314bb2084a96854535dde897a5ae
Source dataset
uspto-grants-1976_02
Patent number
US03940402

Reaction notes

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