4'-Hydroxyacetophenone → HCID 97793、化合物

HRID 1157971ノート

反応式

HRID 1157971 の反応式
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[OH-].[Na+]>CO>[OH:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH:1]=[CH:17][C:16]2[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 74694'-HydroxyacetophenoneHCID 14798Sodium HydroxideHCID 312444-Methoxybenzaldehyde

生成物 1

HCID 97793HCID 97793、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a well-stirred solution of 4-hydroxy acetophenone, 1 (10 g, 73.5 mmol) and 4-methoxy benzaldehyde, 4 (8.9 mL, 73.5 mmol) in methanol (140 mL) was added 50% w/v aqueous sodium hydroxide solution (70 mL). The reaction mixture was stirred at room temperature for 12 h and then evaporated in vacuo. Water was added and acidified with hydrochloric acid (1N) and extracted with ethyl acetate. The organic layer was separated, washed with water, dried over sodium sulphate, filtered and evaporated in vacuo. The residue yielded pure 7 after purification by column chromatography. Yield 16.8 g (90%); mp 184-185° C. MS (EI) m/z 254 (M+, 100%), 253 (34.7%), 239 (32.3%), 161 (36.8%), 121 (79.5%); IR (KBr) 3371, 1654; 1H NMR (200 MHz, CDCl3) δ 7.99 (d, J=8.6 Hz, 2H), 7.78 (d, J=15.6 Hz, 1H), 7.60 (d, J=8.6 Hz, 2H), 7.41 (d, J=15.6 Hz, 1H), 6.93 (d, J=7.2 Hz, 4H), 5.85 (s, 1H), 3.86 (s, 3H).

後処理

  1. customevaporated in vacuo
  2. additionWater was added
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue yielded pure 7
  10. customafter purification by column chromatography

出典と根拠

ORDレコード
ord-80656075132a4f398a172559e79d2929
出典データセット
uspto-grants-2010_10
特許番号
US07807712B2

反応ノート

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