Dimethylformamide → p-[(2-Methyl-2-norbornyl]oxy)nitrobenzene

HRID 66094

Reaction equation

HRID 66094 reaction equation
[CH2:1]1[CH:5]2[CH2:6][CH:7]([OH:8])[CH:3]([CH2:4]2)[CH2:2]1.[CH3:9]N(C=O)C.[H-].[Na+].F[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1>C1C=CC=CC=1>[CH3:9][C:7]1([O:8][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[CH2:6][CH:5]2[CH2:4][CH:3]1[CH2:2][CH2:1]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 790282-Norbornanol

Product 1

HCID 70588011p-[(2-Methyl-2-norbornyl]oxy)nitrobenzene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 15.6 g. (0.10 mole) of the crude norborneol in 80 ml. DMF and 160 ml. C6H6 there was added 4.21 g. of 56% NaH dispersion. Following 30 minutes heating at reflux, there was added 14.1 g. of p-fluoronitrobenzene. The mixture was then heated for an additional 6 hours, cooled and washed thoroughly with H2O and brine. The residue was chromatographed on 2 L silica gel (elution with 1:1 SSB:C6H6). Those fractions which showed a single spot on tlc were combined to afford 13.5 g. of product as a yellow oil; the NMR is in agreement with the structure.

Workup

  1. temperatureheating
  2. temperatureat reflux
  3. additionthere was added 14.1 g
  4. temperatureThe mixture was then heated for an additional 6 hours
  5. temperaturecooled
  6. washwashed thoroughly with H2O and brine
  7. customThe residue was chromatographed on 2 L silica gel (elution with 1:1 SSB:C6H6)
  8. customto afford 13.5 g

Sources & evidence

ORD record
ord-3356b2cd294448be9c04bd9d6f95154f
Source dataset
uspto-grants-1978_12
Patent number
US04130561

Linked notes

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