Acetyl chloride → 2-(4'-Fluoro-4-biphenylyl)-3-octyn-2-ol

HRID 26715

Reaction equation

HRID 26715 reaction equation
[H-].[Na+].C#CCCCC.FC1C=CC(C2C=CC(C(=O)C)=CC=2)=CC=1.FC1C=CC(C2C=CC=CC=2)=CC=1.C(Cl)(=O)C.[Al+3].[Cl-].[Cl-].[Cl-].[F:46][C:47]1[CH:52]=[CH:51][C:50]([C:53]2[CH:58]=[CH:57][C:56]([C:59]([O-:67])([C:61]#[C:62][CH2:63][CH2:64][CH2:65][CH3:66])[CH3:60])=[CH:55][CH:54]=2)=[CH:49][CH:48]=1.[Na+].[Cl-].[NH4+]>C1COCC1>[F:46][C:47]1[CH:48]=[CH:49][C:50]([C:53]2[CH:58]=[CH:57][C:56]([C:59]([OH:67])([C:61]#[C:62][CH2:63][CH2:64][CH2:65][CH3:66])[CH3:60])=[CH:55][CH:54]=2)=[CH:51][CH:52]=1

Participants

10

Reactant 8

HCID 6367Acetyl chlorideHCID 94614-FluorobiphenylHCID 127321-HexyneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 6081141-(4'-Fluoro(1,1'-biphenyl)-4-yl)ethanoneHCID 6451240Aluminum(III) ChlorideHCID 23684843Sodium 2-(4'-fluoro-4-biphenylyl)-3-octyn-2-olate

Product 1

HCID 213223242-(4'-Fluoro-4-biphenylyl)-3-octyn-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.43 g. of sodium hydride in added portionwise to a solution of 8.2 g. of 1-hexyne in 30 ml. of dry THF and then, under a stream of nitrogen, a solution of 21.4 g. of 4'-fluoro-4-acetylbiphenyl, preparable from 4-fluorobiphenyl and acetyl chloride in the presence of AlCl3, in 60 ml. of THF is added thereto. The reaction mixture contains sodium 2-(4'-fluoro-4-biphenylyl)-3-octyn-2-olate. It is hydrolyzed with an aqueous 15% ammonium chloride solution and worked up as usual. There is obtained 2-(4'-fluoro-4-biphenylyl)-3-octyn-2-ol; m.p. 62°.

Sources & evidence

ORD record
ord-d8e24277f179448da92e833593cde990
Source dataset
uspto-grants-1979_04
Patent number
US04151294

Linked notes

Loading…