3,4-Dihydroxybenzaldehyde → 3,4-dihexyloxybenzaldehyde

HRID 270638ノート

反応式

HRID 270638 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 118229373,4-dihexyloxybenzaldehyde収率 161%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bca58000c6ac481aa891a9aacefb0a86
出典データセット
uspto-grants-2008_11
特許番号
US07449578B1

反応ノート

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