2',4'-Dihydroxyacetophenone → Acetic acid 3-(2,4-dimethoxyphenyl)-7-hydroxy4-methyl-2-oxo-2H-chromen-7-yl ester

HRID 2214288

反応式

HRID 2214288 の反応式
[CH3:1][C:2]([C:4]1[CH:5]=CC(O)=[CH:8][C:9]=1O)=O.[CH3:12][O:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[CH2:22][C:23]([OH:25])=[O:24].[C:26]([O:29][C:30](=[O:32])[CH3:31])(=[O:28])[CH3:27].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[CH:22]1[C:9]([CH3:8])=[C:4]2[C:5](=[CH:27][C:26]([O:29][C:30](=[O:32])[CH3:31])([OH:28])[CH:1]=[CH:2]2)[O:24][C:23]1=[O:25]

参加物

6

反応物 5

HCID 69902',4'-DihydroxyacetophenoneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 3505552-(2,4-Dimethoxyphenyl)acetic acidHCID 516892Sodium Bicarbonate

生成物 1

HCID 69317693Acetic acid 3-(2,4-dimethoxyphenyl)-7-hydroxy4-methyl-2-oxo-2H-chromen-7-yl ester

実験手順

A mixture of 2,4-dihydroxyacetophenone (2.233 g, 14.67 mmol, 1 eq), 2, 4-dimethoxyphenylacetic acid (2.88 g, 14.67 mmol, 1 eq), acetic anhydride (7.5 mL, 78 mmol, 5 eq) and triethylamine (1.49 mL, 2.05 mmol, 1 eq) was stirred and heated to reflux under nitrogen for 48 hours. After cooling to room temperature the dark syrupy reaction mixture was poured into ice water (˜450 mL). The suspension of sticky, semisolid product was neutralized by slowly adding solid NaHCO3 to the mixture. The mixture was then allowed to solidify overnight. The dark solid was isolated by filtration, washed with water, sucked dry, and recrystallized from acetic acid to yield the title compound as an ivory crystalline solid. A second crop (0.95g, 18.3%) was isolated from the mother liquor.

後処理

  1. temperatureheated
  2. temperatureto reflux under nitrogen for 48 hours
  3. additionThe suspension of sticky, semisolid product
  4. customThe dark solid was isolated by filtration
  5. washwashed with water
  6. customsucked dry
  7. customrecrystallized from acetic acid

出典と根拠

ORDレコード
ord-d0b4a446905740748be34967163ece0e
出典データセット
uspto-grants-2006_09
特許番号
US07105679B2

関連ノート

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