Water → HCID 20566686, compound

HRID 2163120Notes

Reaction equation

HRID 2163120 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-])=O)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]=[N:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 746741-tert-Butyl-2-nitrobenzeneHCID 21226445Aluminium lithium hydride

Product 1

HCID 20566686HCID 20566686, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2-t-Butylnitrobenzene (30.0grams, 0.17 mole) in 100 milliliters of ether was added to a suspension of 8.22 grams (0.22 mole) of lithium aluminum hydride in 700 milliliters of ether at a temperature of 5 - 10° C. The mixture was allowed to come to ambient temperature and stirred for an additional 0.5-hour period. Hydrolysis was accomplished by the successive addition of 15 milliliters of water, 15 milliliters of 20 percent aqueous sodium hydroxide, and 30 milliliters of water. After mixing for 2 hours, the inorganic salts were removed by filtration and the ether evaporated. The residue was applied to an activated neutral alumina column (200 grams, 80-200 mesh) and eluted with hexane at a flow rate of 10 drops per minute. The initial fractions (about 700 milliliters) were discarded and the product, a bright red band on the column, was collected. Evaporation of the hexane followed by crysta-lization of the residue from ethanol gave 4.6 grams (18.7 percent) of 2,2'-di-t-butylazobenzene melting point, 90-91° C.

Workup

  1. customto come to ambient temperature
  2. customHydrolysis
  3. additionAfter mixing for 2 hours
  4. customthe inorganic salts were removed by filtration
  5. customthe ether evaporated
  6. washeluted with hexane at a flow rate of 10 drops per minute
  7. customthe product, a bright red band on the column, was collected
  8. customEvaporation of the hexane

Sources & evidence

ORD record
ord-14cc14f860fd40e8886da680e867d866
Source dataset
uspto-grants-1979_01
Patent number
US04132611

Reaction notes

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