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

HRID 866047

반응식

HRID 866047 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+].[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

참가 물질

5

반응물 3

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

생성물 1

HCID 795263,4-Bis(benzyloxy)benzaldehyde

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5b35fb480172456d85fac5fe8ed8a2d3
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05569786

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