Methanol → 2,2-Dinitro-1-methoxy-1-phenylpropane

HRID 27290Notes

Reaction equation

HRID 27290 reaction equation
[Na].[N+:2]([C:5]([CH3:13])=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([O-:4])=[O:3].[N+:14](C([N+]([O-])=O)([N+]([O-])=O)[N+]([O-])=O)([O-:16])=[O:15].[CH3:27][OH:28]>>[N+:2]([C:5]([N+:14]([O-:16])=[O:15])([CH3:13])[CH:6]([O:28][CH3:27])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([O-:4])=[O:3]

Participants

5

Reactant 4

HCID 887Methanol2×HCID 10509TetranitromethaneHCID 128072-Nitro-1-phenylpropeneHCID 5360545Sodium

Product 1

HCID 124231122,2-Dinitro-1-methoxy-1-phenylpropane

Procedure

1.15 g (0.05 mol) of sodium metal dissolved in 75 ml of methanol was added dropwise with cooling (0°-10° C.) a solution of 4.0 g (0.025 mol) of 2-nitro-1-phenyl-1-propene and 4.9 g (0.025 mol) of tetranitromethane in 25 ml of methanol. The resulting solution was stirred at room temperature for 1 hour. The product was isolated and purified as described in Example 1 above, except that acidification prior to workup was omitted. Ultimately there was obtained 2.5 g (42%) of analytically pure, white crystalline 2,2-dinitro-1-methoxy-1-phenylpropane, mp 53°-55° C. The same procedure was employed to prepare the 2-ethoxy and 2-propoxy derivatives with the exception that the appropriate alcohol was substituted for methanol.

Workup

  1. additionwas added dropwise
  2. customThe product was isolated
  3. custompurified

Sources & evidence

ORD record
ord-3f60ac84ec99431fafebf101de454601
Source dataset
uspto-grants-1980_09
Patent number
US04220804

Reaction notes

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