Pyridinium chloride → 1-(2'-Ethyl-5'-hydroxy-2-propylbiphenyl-4-yl)-1-propanone
Reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9]C)=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:20])[CH2:18][CH3:19])=[CH:13][C:12]=1[CH2:21][CH2:22][CH3:23])[CH3:2].Cl.N1C=CC=CC=1>O>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:20])[CH2:18][CH3:19])=[CH:13][C:12]=1[CH2:21][CH2:22][CH3:23])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
413 g (1.33 mol) of 1-(2′-ethyl-5′-methoxy-2-propylbiphenyl-4-yl)propan-1-one and 768 g (6.64 mol) of pyridine hydrochloride are placed in a round-bottomed flask. The mixture is heated at 160°-170° C. for 4 hours with stirring. The reaction medium is allowed to return to 100°-110° C. and 800 ml of water are added. The mixture is cooled to 30° C. and extracted with 1.6 liters of ethyl acetate. After separating by settling, the aqueous phase is extracted with 600 ml of ethyl acetate. The organic phases are combined and washed twice with 800 ml of water. After evaporating under reduced vacuum, 410 g of 1-(2′-ethyl-5′-hydroxy-2-propylbiphenyl-4-yl)propan-1-one are obtained in the form of an oil.
Workup
- temperatureThe mixture is heated at 160°-170° C. for 4 hours
- customto return to 100°-110° C.
- extractionextracted with 1.6 liters of ethyl acetate
- customAfter separating
- extractionthe aqueous phase is extracted with 600 ml of ethyl acetate
- washwashed twice with 800 ml of water
- customAfter evaporating under reduced vacuum, 410 g of 1-(2′-ethyl-5′-hydroxy-2-propylbiphenyl-4-yl)propan-1-one
- customare obtained in the form of an oil
Sources & evidence
- ORD record
- ord-b1fbc9cd125b4ec9b0e327045166c247
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07638657B2
Reaction notes
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