Reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[C:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=[O:7]>C(O)C>[Cl:3][C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[CH:6]([C:8]1[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=1)[OH:7]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Under a nitrogen atmosphere, 1.7 grams ( 0.044 mole) of sodium borohydride pellets was added to 100 ml of stirred ethanol. To this was added 10.0 grams (0.040 moles) of 2,4′-dichlorobenzophenone in one portion. Upon completion of the addition the reaction mixture was stirred at ambient temperature for about 18 hours. After this time the ethanol was removed under reduced pressure, and the resulting residue was taken up in 250 mL of aqueous 5% sodium hydroxide solution. The solution was extracted with two 100 mL portions of diethyl ether. The combined ether extracts were washed with aqueous saturated sodium chloride solution. The organic layer was filtered and the filtrate concentrated under reduced pressure, yielding 9.5 grams of (2-chlorophenyl)(4-chlorophenyl)methanol. The NMR spectrum was consistent with the proposed structure.
Workup
- additionUpon completion of the addition the reaction mixture
- customAfter this time the ethanol was removed under reduced pressure
- extractionThe solution was extracted with two 100 mL portions of diethyl ether
- washThe combined ether extracts were washed with aqueous saturated sodium chloride solution
- filtrationThe organic layer was filtered
- concentrationthe filtrate concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-f24d825a1a7a4898832b40653c000954
- Source dataset
- uspto-grants-2001_12
- Patent number
- USH0002007H1
Linked notes
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