Benzene → 4-Nitro-1,1'-biphenyl

HRID 1719795Notes

Reaction equation

HRID 1719795 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7](N)=[CH:6][CH:5]=1)([O-:3])=[O:2].ClC(Cl)(Cl)C(O)=O.COC(OC)OC.[CH:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.N([O-])=O.[Na+].Cl>O>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

8

Reactant 6

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 6421Trichloroacetic AcidHCID 74754-NitroanilineHCID 9005Trimethyl orthoformateHCID 23668193Sodium Nitrite

Product 1

HCID 71144-Nitro-1,1'-biphenylYield 106.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-nitro-aniline (3.77 g; 0.0273 mole), trichloroacetic acid (6 g; 0.0367 mole), cuprous chloride (0.14 g; 0.0014 mole) and trimethylorthoformate (5.8 g; 0.0548 mole) in benzene (140.6 g; 1.8 mole) was heated to 60° C. Aliquots of sodium nitrite (2.3 g; 0.0333 mole) were added to the thus obtained mixture. The mixture was maintained under stirring for 22 hours at 60° C. and then hydrolyzed with water and diluted hydrochloric acid. The organic layer was separated, washed with water and concentrated. Crystallization of the residue from methanol afforded 5.8 g of 4-nitro-biphenyl, melting at 114°-116° C. Yield, 80%.

Workup

  1. temperatureThe mixture was maintained
  2. customThe organic layer was separated
  3. washwashed with water
  4. concentrationconcentrated
  5. customCrystallization of the residue from methanol

Sources & evidence

ORD record
ord-10223a4ad1294bceb0d16b4ff9e9e641
Source dataset
uspto-grants-1985_09
Patent number
US04542233

Reaction notes

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