ST4026352 → Benzene-1,3-diylbis[(4-hydroxyphenyl)methanone]

HRID 333206노트

반응식

HRID 333206 반응식
C[O:2][C:3]1[CH:26]=[CH:25][C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:24])[C:16]3[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=3)[CH:10]=2)=[O:8])=[CH:5][CH:4]=1.CSC.B(F)(F)F>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:24])[C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[CH:10]=2)=[O:8])=[CH:25][CH:26]=1

참가 물질

4

반응물 2

HCID 344097ST4026352HCID 11137191Trifluoroborane-methyl sulfide

생성물 1

HCID 228420Benzene-1,3-diylbis[(4-hydroxyphenyl)methanone]수율 38%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a well-stirred solution of 1,3-bis-(4-methoxybenzoyl)benzene 14 (1.80 g, 5.2 mmol) in dichloromethane (85 mL) was added boron trifluoride dimethyl sulfide complex (BF3.SMe2, 15 mL). The mixture was stirred for 27 h. After the reaction was quenched by water, the mixture was extracted with ethyl acetate (3×80 mL). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated under vacuum. The resulting solid was further purified using flash chromatography (silica gel, hexanes:ethyl acetate, 50:50) to afford the pure 1,3-bis-(4-hydroxybenzoyl)benzene 20 (0.62 g, 1.95 mmol) as a white solid in a 38% yield; 1H NMR (500 MHz, Acetone-d6): δ 9.28 (s, OH), 8.04 (td, J=1.7 Hz, 1.3 Hz, 1H, ArH), 7.98 (dd, J=7.7 Hz, 1.75 Hz, 2H, ArH), 7.80 (ddd, J=9.5 Hz, 4.8 Hz, 2.75 Hz, 4H, ArH), 7.73 (td, J=7.9 Hz, 0.45 Hz, 1H, ArH), 7.00 (ddd, J=9.5 Hz, 4.8 Hz, 2.75 Hz, 4H, ArH).

후처리

  1. customAfter the reaction was quenched by water
  2. extractionthe mixture was extracted with ethyl acetate (3×80 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe resulting solid was further purified

출처 및 근거

ORD 기록
ord-ce94d7cd33b94bbe9868141411e52270
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877967B2

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