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

HRID 333206ノート

反応式

HRID 333206 の反応式
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

参加物

4

反応物 2

HCID 344097ST4026352HCID 11137191Trifluoroborane-methyl sulfide

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ce94d7cd33b94bbe9868141411e52270
出典データセット
uspto-grants-2014_11
特許番号
US08877967B2

反応ノート

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