Desoxyanisoin → 1,2-Bis(4-hydroxyphenyl)ethanone

HRID 340855

反応式

HRID 340855 の反応式
[C:1]1([C:9]([CH2:11][C:12]2[CH:19]=[CH:18][C:15]([O:16]C)=[CH:14][CH:13]=2)=[O:10])[CH:8]=[CH:7][C:4]([O:5]C)=[CH:3][CH:2]=1.Cl.N1C=CC=CC=1>O>[OH:5][C:4]1[CH:7]=[CH:8][C:1]([C:9]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([OH:16])=[CH:18][CH:19]=2)=[O:10])=[CH:2][CH:3]=1

参加物

4

反応物 2

HCID 67120DesoxyanisoinHCID 10176127Pyridinium chloride

生成物 1

HCID 134272011,2-Bis(4-hydroxyphenyl)ethanone収率 85.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
200 °C

実験手順

Desoxyanisoin (5.00 g, 19.5 mmol) and pyridine hydrochloride (9.02 g, 78.0 mmol) were added to a round-bottom flask equipped with a condenser. The mixture was refluxed for 5 h at 200° C., cooled to room temperature, and poured into water. The precipitate was filtered and recrystallized from acetic acid to give 3.8 g (85% yield) of a pale yellow crystalline solid. 1H NMR (DMSO-d4, 300 MHz, ppm): 10.35 (s, 1H, HO—Ar—CO), 9.28 (s, 1H, HO—Ar—CH2), 7.91 (d, 2H, J=8.7 Hz, Ar—H), 7.04 (d, 2H, J=8.5 Hz, Ar—H), 6.84 (d, 2H, J=8.7 Hz, Ar—H), 6.68 (d, 2H, J=8.5 Hz, Ar—H), 4.11 (s, 2H, Ar—CO—CH2—Ar). 13C NMR (DMSO-d6, 75 MHz, ppm): 196.5, 162.3, 156.2, 131.3, 130.7, 128.1, 125.9, 115.5, 115.4, 43.7.

後処理

  1. customequipped with a condenser
  2. temperaturecooled to room temperature
  3. filtrationThe precipitate was filtered
  4. customrecrystallized from acetic acid

出典と根拠

ORDレコード
ord-f018fbdc7d9e46c9adabfc3656331347
出典データセット
uspto-grants-2014_11
特許番号
US08895688B2

関連ノート

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