Butanedione → 3-Hydroxy-3-phenylbutan-2-one

HRID 246882

Reaction equation

HRID 246882 reaction equation
O1CCCC1.C1(C)C=CC=CC=1.[C:13]1([Mg]Br)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:21][C:22](=[O:26])[C:23](=[O:25])[CH3:24]>C1COCC1.C1(C)C=CC=CC=1>[OH:26][C:22]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:21])[C:23](=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 650ButanedioneHCID 1140TolueneHCID 8028TetrahydrofuranHCID 178418255HCID 178418255, compound

Product 1

HCID 2332203-Hydroxy-3-phenylbutan-2-oneYield 68%

Reagents, catalysts & solvents 1

HCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

The process can also be run in mixtures of tetrahydrofuran and toluene, thereby making the process more economical. When 1.1 equivalent of phenylmagnesium bromide (1.9M in 50% THF/PhMe) was added to 2,3-butanedione in 50% THF/PhMe, crude product was isolated in 82.4% yield (Run 10, Table IV) after work-up. Short path vacuum distillation gave 3-hydroxy-3-phenylbutan-2-one in 68% yield. Alternatively, preparation of phenylmagnesium bromide in 38% THF/PhMe, followed by reaction with 2,3-butanedione in 38% THF/PhMe afforded 3-hydroxy-3-phenylbutan-2-one in 66.4% yield (Run 11, Table IV) after work-up and distillation. Similarly phenylmagnessium bromide in 25% THR/PheMe reacted with 2,3-butanedione in 25% THF/PheMe yielded 3-hydroxy-3-phenylbutan-2-one in 56.9% yield after work-up and distillation.

Workup

  1. customcrude product was isolated in 82.4% yield (Run 10, Table IV) after work-up
  2. distillationShort path vacuum distillation

Sources & evidence

ORD record
ord-cede89cb38c04486bb9c278853a2f81c
Source dataset
uspto-grants-1987_11
Patent number
US04704475

Linked notes

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