Potassium Carbonate → 2-((E)-3,7-dimethylocta-2,6-dienyloxy)-6-methoxybenzaldehyde

HRID 30094

反応式

HRID 30094 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]=[O:5].[CH2:12](Br)/[CH:13]=[C:14](/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])\[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:15]/[C:14](/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])=[CH:13]\[CH2:12][O:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]=[O:5]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 696926-MethoxysalicylaldehydeHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-

生成物 1

HCID 597893412-((E)-3,7-dimethylocta-2,6-dienyloxy)-6-methoxybenzaldehyde

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-hydroxy-6-methoxybenzaldehyde (4.72 g, 30.43 mmol) in dry DMF (50 ml) was added geranyl bromide (7.5 g, 33.50 mmol) followed by solid potassium carbonate (5.5 g, 39.86 mmol). The mixture was stirred at room temperature for 48 h. The suspension was filtered through a layer of dry sodium sulfate (top) and silica gel (bottom), washed with 200 ml ethyl acetate and decanted into a separatory funnel. The mixture was washed sequentially with aqueous ammonium chloride, water (twice), brine, and the organic phase was dried over Na2SO4. The solution was concentrated in vacuo on a rotovap. The brown gel material was then purified by chromatography via silica gel using 8:2 hexanes:ethyl acetate eluent to provide 2-((E)-3,7-dimethylocta-2,6-dienyloxy)-6-methoxybenzaldehyde as pale yellow oil.

後処理

  1. filtrationThe suspension was filtered through a layer of dry sodium sulfate (top) and silica gel (bottom)
  2. washwashed with 200 ml ethyl acetate
  3. customdecanted into a separatory funnel
  4. washThe mixture was washed sequentially with aqueous ammonium chloride, water (twice), brine
  5. dry with materialthe organic phase was dried over Na2SO4
  6. concentrationThe solution was concentrated in vacuo on a rotovap
  7. customThe brown gel material was then purified by chromatography via silica gel using 8:2 hexanes

出典と根拠

ORDレコード
ord-888504b2d96044d1a3f5147db57b2942
出典データセット
uspto-grants-2008_09
特許番号
US07423045B2

関連ノート

読み込み中…