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

HRID 30094

반응식

HRID 30094 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-888504b2d96044d1a3f5147db57b2942
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423045B2

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