Formic Acid → 4-(4'-Fluoro-4-biphenylyl)-4-hydroxy-butyric acid

HRID 2397405Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[OH-].[Na+].C(O)=O>O1CCCC1.CCOCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([OH:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 2.75 gm (0.01 mol) of 4-(4'-fluoro-4-biphenylyl)-4-oxo-butyric acid in 50 ml of absolute tetrahydrofuran 0.20 gm (0.005 mol) of lithiumaluminumhydride in 50 ml of absolute tetrahydrofuran was added dropwide, while stirring and cooling at -20° C. After stirring for 4 hours at -20° C., the reaction mixture was poured into ice water and acidified with aqueous 50% sulfuric acid. Subsequently, the mixture was made alkaline by adding aqueous 20% sodium hydroxide, and was again acidified with formic acid. The precipitated semi-solid product was dissolved in ether, and after evaporating the ether, the crystalline residue was dissolved in acetone. From this solution the cyclohexylamine salt of 4-(4'-fluoro-4-biphenylyl)-4-hydroxy-butyric acid was precipitated by addition of cyclohexylamine, and the salt was recrystallized from ethyl acetate/absolute ethanol. Melting point 176°-178° C. (decomp.); yield: 2.2 gm.

Workup

stirringAfter stirring for 4 hours at -20° C.
customafter evaporating the ether
dissolutionthe crystalline residue was dissolved in acetone
customFrom this solution the cyclohexylamine salt of 4-(4'-fluoro-4-biphenylyl)-4-hydroxy-butyric acid was precipitated by addition of cyclohexylamine
customthe salt was recrystallized from ethyl acetate/absolute ethanol

Sources & evidence

ORD record: ord-3c656a2283914b688ecade3a6580e3a2
Source dataset: uspto-grants-1977_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04021479

Reaction notes

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