Benzyl Bromide → 3,4-Bis(benzyloxy)benzaldehyde

HRID 866047

反応式

HRID 866047 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+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[CH2:17]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:14][CH2:11][C:2]1[CH:3]=[CH:4][CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium Carbonate

生成物 1

HCID 795263,4-Bis(benzyloxy)benzaldehyde

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of 3,4-dihydroxy-benzaldehyde (2.76 g, 20 mmol) in dry acetone (50 ml), potassium carbonate (5.52 g, 40 mmol) and benzylbromide (5 ml, 42 mmol) was heated at reflux for 12 hours. The mixture was cooled to room temperature, potassium carbonate was removed by filtering the solution and the filtrate was concentrated to a powder which was recrystallized from acetone to yield (5.4 g, 81%) ether as prisms, mp 89°-90° (lit. mp 90°) IR νmax 1685, 1595, 1483, 1508, 1454, 1434, 1269, 1132, 695, 650 cm-1 ; 1H-NMR (90 MHz), 5.21 (2H, s, ArCH2O), 5.26 (2H, s, ArCH20), 7.02 (1H, d, J=7.9 Hz), 7.30-7.50 (12H, ArH), 9.81 (1H, s, CHO). Anal. calcd for C21H18O3 : C, 79.23; H, 5.70. Found: C, 79.26; H, 5.68.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 12 hours
  3. custompotassium carbonate was removed
  4. filtrationby filtering the solution
  5. concentrationthe filtrate was concentrated to a powder which
  6. customwas recrystallized from acetone
  7. customto yield (5.4 g, 81%) ether as prisms, mp 89°-90° (lit. mp 90°) IR νmax 1685, 1595, 1483, 1508, 1454, 1434, 1269, 1132, 695, 650 cm-1

出典と根拠

ORDレコード
ord-5b35fb480172456d85fac5fe8ed8a2d3
出典データセット
uspto-grants-1996_10
特許番号
US05569786

関連ノート

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