Piperidine → HCID 20324267, compound
Reaction equation
[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([C:12]#[CH:13])([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.N1CCCCC1.[H][H]>[Ni].O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C.CO>[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([CH:12]=[CH2:13])([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1Participants
Procedure
22.6 g. 2-fluoro-α-ethynyl-benzhydrol and 0.74 g. of zinc acetate dihydrate are dissolved in a mixture of 260 ml. of methanol and 10 ml. of piperidine, and 4.4 g. of Raney-nickel catalyst are added to the mixture. The reaction mixture is hydrogenated at room temperature under atmospheric pressure until the uptake of the calculated amount of hydrogen. Thereafter the catalyst is filtered off, and the solvent is evaporated in vacuo. The residue is dissolved in benzene, and the solution is washed with water in order to remove zinc acetate. The benzene phase is dried over anhydrous magnesium sulfate, filtered, and evaporated. The residual oil is distilled at 0.05 mmHg. 21.4 g. of colorless, oily 2-fluoro-α-vinyl-benzhydrol are obtained; b.p.: 91°-93° C/0.05 mmHg.
Workup
- filtrationThereafter the catalyst is filtered off
- customthe solvent is evaporated in vacuo
- dissolutionThe residue is dissolved in benzene
- washthe solution is washed with water in order
- customto remove zinc acetate
- dry with materialThe benzene phase is dried over anhydrous magnesium sulfate
- filtrationfiltered
- customevaporated
- distillationThe residual oil is distilled at 0.05 mmHg
Sources & evidence
- ORD record
- ord-91e3a890b63e47af8757fc3f13c10556
- Source dataset
- uspto-grants-1978_06
- Patent number
- US04094908
Reaction notes
Loading…