Ethanol → 4-Chloro-4'-thiocyanatomethylbenzophenone

HRID 2102

Reaction equation

Br[CH2:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.[S-:18][C:19]#[N:20].[Na+].C(O)C>C(OCC)(=O)C>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]([C:6]2[CH:16]=[CH:17][C:3]([CH2:2][S:18][C:19]#[N:20])=[CH:4][CH:5]=2)=[O:8])=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 60 °C

Procedure

4-bromomethyl-4'-chlorobenzophenone (5.7 g) and sodium thiocyanate (5.5 g) were added to ethanol (50 ml), and the mixture was stirred for one hour at 60° C. The reaction mixture was concentrated, and water was added to the residue. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. The residual solid was washed with a solvent mixture of n-hexane:ethyl acetate=10:1 to obtain the desired product (2.2 g, melting point: 129° to 131° C., yield:42%).

Workup

concentrationThe reaction mixture was concentrated
additionwater was added to the residue
extractionThe mixture was extracted with ethyl acetate
washThe ethyl acetate layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationEthyl acetate was distilled off under reduced pressure
washThe residual solid was washed with a solvent mixture of n-hexane

Sources & evidence

ORD record: ord-39af67312f5442e6ae004f66e6de33ad
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05728699

Linked notes

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