3,4-Dihydroxybenzaldehyde → 3,4-dihexyloxybenzaldehyde

HRID 270638노트

반응식

HRID 270638 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1O)[CH:5]=[O:6].[C:11]([O-:14])([O-])=O.[K+].[K+].I[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>C(O)CCC>[CH2:18]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:14][CH2:11][CH2:8][CH2:9][CH2:2][CH2:3][CH3:4])[CH:5]=[O:6])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

참가 물질

5

반응물 3

HCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 125271-Iodohexane

생성물 1

HCID 118229373,4-dihexyloxybenzaldehyde수율 161%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

3,4-Dihydroxy-benzaldehyde (2.1 g, 0.015 mol), K2CO3 (4.0 g, 0.03 mol) and 1-iodohexane (6.4 g, 0.03 mol) were stirred in 100 ml of 1-butanol under reflux for 24 h. After cooling, the 1-butanol was removed by rotary evaporation. The residue was dissolved in 200 ml of ether, washed with water (dist.) and brine. The solution was dried over Na2SO4 and the solvent was removed to yield 3.7 g 3,4-Bis-hexyloxy-benzaldehyde (85%) as a dark solid. 1H NMR (400 MHz, CDCl3): δ 9.83 (s, 1H), 7.41 (m, 2H), 6.95 (d, 1H, J=8.5 Hz), 4.07 (m, 4H), 1.85 (m, 4H), 1.48 (m, 4H), 1.35 (m, 8H), 0.91 (m, 6H).

후처리

  1. temperatureunder reflux for 24 h
  2. temperatureAfter cooling
  3. customthe 1-butanol was removed by rotary evaporation
  4. dissolutionThe residue was dissolved in 200 ml of ether
  5. washwashed with water (dist.) and brine
  6. dry with materialThe solution was dried over Na2SO4
  7. customthe solvent was removed

출처 및 근거

ORD 기록
ord-bca58000c6ac481aa891a9aacefb0a86
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449578B1

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