4-Chlorobenzophenone → 4-Chlorobenzhydrol

HRID 1032602

Reaction equation

HRID 1032602 reaction equation
[C:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>O1CCCC1.CO>[Cl:15][C:12]1[CH:11]=[CH:10][C:9]([CH:7]([OH:8])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 86534-ChlorobenzophenoneHCID 4311764Sodium borohydride

Product 1

HCID 84014-ChlorobenzhydrolYield 93.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

15.2 g (0.07 mole) of phenyl-(4-chlorophenyl)-ketone are dissolved in 30 ml of tetrahydrofuran and 10 ml of methanol. 1.32 g (0.035 mole) of sodium borohydride are gradually added, with stirring, and the exothermic reaction is maintained between 25° and 30° C. by cooling. After one hour ketone can no longer be detected by thin layer chromatography. The mixture is then extracted with water and chloroform, the chloroform is dried with sodium sulfate and removed in a rotary evaporator. The crude yield is 16.2 g (oil). Of this 15.5 g are distilled at 220° C. and 30 mbar in a bulb tube oven. 14.3 g of an oil are obtained which is more than 95% pure according to gas chromatography and solidifies into crystals on cooling. 13.3 g are recrystallised from a mixture of 25 ml of n-hexane and 5 ml of cyclohexane. The yield is 12.2 g; m.p. 58°-60° C.

Workup

  1. customthe exothermic reaction
  2. temperatureis maintained between 25° and 30° C.
  3. temperatureby cooling
  4. extractionThe mixture is then extracted with water and chloroform
  5. dry with materialthe chloroform is dried with sodium sulfate
  6. customremoved in a rotary evaporator
  7. distillationOf this 15.5 g are distilled at 220° C.

Sources & evidence

ORD record
ord-432839f0d75b48308e78fd9b815d2b51
Source dataset
uspto-grants-1990_09
Patent number
US04959096

Linked notes

Loading…