Benzyl Bromide → 5-(Benzyloxy)-2-methoxybenzaldehyde

HRID 346324

反応式

HRID 346324 の反応式
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].ClCCl.O>[CH2:12]([O:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

7

反応物 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 3583415-Hydroxy-2-Methoxybenzaldehyde

生成物 1

HCID 109666945-(Benzyloxy)-2-methoxybenzaldehyde収率 91%

試薬・触媒・溶媒 3

HCID 21218Trioctylmethylammonium chloride触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred suspension of 5-hydroxy-2-methoxybenzaldehyde (306.6 g, prepared by the method of Ulrich et al, J. Org. Chem., 1974, 39, 2437), benzyl bromide (355.8 g) and Adogen 464 (48.5 g) in dichloromethane (600 ml) was added a solution of sodium hydroxide (123.5 g) in water (500 ml). The mixture became warm and the suspension dissolved; additional dichloromethane (300 ml) was added to prevent crystallisation of the benzylated product. After 2 hours, the organic layer was removed, washed twice with water, once with saturated sodium chloride solution, then dried with anhydrous magnesium sulphate The solution was concentrated, then treated with petroleum spirit to give 5-benzyloxy-2-methoxybenzaldehyde (445.7 g, 91%), m.p. 99-100°.

後処理

  1. customprepared by the method of Ulrich et al, J
  2. temperatureThe mixture became warm
  3. dissolutionthe suspension dissolved
  4. customcrystallisation of the benzylated product
  5. customthe organic layer was removed
  6. washwashed twice with water, once with saturated sodium chloride solution
  7. dry with materialdried with anhydrous magnesium sulphate The solution
  8. concentrationwas concentrated
  9. additiontreated with petroleum spirit

出典と根拠

ORDレコード
ord-acb2eb4a36574384ae2cede7d79fd45d
出典データセット
uspto-grants-1991_10
特許番号
US05061798

関連ノート

読み込み中…