Sodium Hydroxide → 4-Hydroxy-4'-nitrobiphenyl

HRID 2082111Notes

Reaction equation

HRID 2082111 reaction equation
[OH-].[Na+].C([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)(=O)C1C=CC=CC=1>C(O)C>[OH:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2596334'-Nitrobiphenyl-4-yl benzoate

Product 1

HCID 1380784-Hydroxy-4'-nitrobiphenylYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The equivalent amount of a 40% caustic soda solution is added, by drops, to a mixture of 300 g 4-benzoyloxy-4'-nitrobiphenyl (see Example 2) and 1500 ml ethanol; after addition, the mixture is heated under reflux for 30 min and then allowed to stand at room temperature overnight. Subsequently, the sodium salt is filtered off and dried. The free base, i.e. the hydroxy compound, is released by suspension of the sodium salt in water and acidification with half-concentrated hydrochloric acid The raw product is filtered off, washed neutral with water and recrystallized from ethanol (melting point: 204° C.); yield: 80%.

Workup

  1. additionafter addition
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 30 min
  4. filtrationSubsequently, the sodium salt is filtered off
  5. customdried
  6. additionThe free base, i.e. the hydroxy compound, is released by suspension of the sodium salt in water and acidification with half-concentrated hydrochloric acid The raw product
  7. filtrationis filtered off
  8. washwashed neutral with water
  9. customrecrystallized from ethanol (melting point: 204° C.)

Sources & evidence

ORD record
ord-842359b2d6a548aa95fc13999e9aa810
Source dataset
uspto-grants-1993_02
Patent number
US05187237

Reaction notes

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