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

HRID 246882

반응식

HRID 246882 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 22635083Tetrahydrofuran toluene용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-cede89cb38c04486bb9c278853a2f81c
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04704475

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