Salicylaldehyde → 2-[[5-(Acetyloxy)pentyl]oxy]benzaldehyde

HRID 327952

반응식

HRID 327952 반응식
[CH:1]1[CH:2]=[CH:3][C:4]([OH:9])=[C:5]([CH:7]=[O:8])[CH:6]=1.[C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br)(=[O:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:9][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=1[CH:7]=[O:8])(=[O:12])[CH3:11]

참가 물질

5

반응물 3

HCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 851405-Bromopentyl acetate

생성물 1

HCID 199221122-[[5-(Acetyloxy)pentyl]oxy]benzaldehyde수율 43,549.398%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 12.2 g (0.1 mmol) of salicyladehyde, 23 g (0.11 mol) of 5-bromopentyl acetate, 44.2 g (0.3 mol) of anhydrous, granular potassium carbonate, and 700 mL of acetonitrile was stirred and refluxed for 20 hr. After being cooled, the resulting mixture was filtered with suction and the solids were washed well with ether. The filtrate and washes were combined and concentrated in vacuo giving a yellow oil which was purified by flash chromatography on silica gel, eluting with 4:1 hexane-ether. There was obtained 10.9 g (43.6%) of 2-[[5-(acetyloxy)pentyl]oxy]benzaldehyde as an oil.

후처리

  1. temperaturerefluxed for 20 hr
  2. temperatureAfter being cooled
  3. filtrationthe resulting mixture was filtered with suction
  4. washthe solids were washed well with ether
  5. concentrationconcentrated in vacuo
  6. customgiving a yellow oil which
  7. customwas purified by flash chromatography on silica gel
  8. washeluting with 4:1 hexane-ether

출처 및 근거

ORD 기록
ord-96c76a38e9b4404eaa89b1c139393c2e
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05273999

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