Water → 4-Hydroxy-4'-chlorobenzophenone

HRID 1448060Notes

Reaction equation

HRID 1448060 reaction equation
[H-].[Na+].C(=N[OH:11])C1C=CC=CC=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:29])[C:20]2[CH:25]=[CH:24][C:23]([N+]([O-])=O)=[CH:22][CH:21]=2)=[CH:15][CH:14]=1.O>CS(C)=O>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:29])[C:20]2[CH:25]=[CH:24][C:23]([OH:11])=[CH:22][CH:21]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12143(Z)-Benzaldehyde oximeHCID 24758Sodium hydrideHCID 3477714-Chloro-4'-nitrobenzophenone

Product 1

HCID 1235044-Hydroxy-4'-chlorobenzophenone

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
70 °C

Procedure

250 cc of DMSO and 4.8 g sodium hydride are placed in a 500 cc flask and heated at 70° C. for 1 hour, by which time the solution has become clear. A solution of 24.2 g (0.2 mole) of benzaldoxime in 100 cc of DMSO is then added drop by drop. The solution is maintained at 70° C. for 1 hour, then allowed to cool to 15° C. A solution of 26 g (0.1 mole) of 4'-chloro-4-nitrobenzophenone in 150 cc of DMSO is then added. The reaction mixture is stirred for 20 hours at ambient temperature and then poured into acidulated water. The mixture is extracted with ether and then with ether containing 2 N caustic soda. On acidification the product is precipitated. Yield 15 g (65%). Melting point 178° C.

Workup

  1. temperatureThe solution is maintained at 70° C. for 1 hour
  2. temperatureto cool to 15° C
  3. additionpoured
  4. extractionThe mixture is extracted with ether
  5. customOn acidification the product is precipitated

Sources & evidence

ORD record
ord-25c02e6106d4415fa8cc36657beaba19
Source dataset
uspto-grants-1979_12
Patent number
US04179515

Reaction notes

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