4-Hydroxybenzaldehyde → 4-[(2,6-dichlorobenzyl)oxy]benzaldehyde

HRID 411737ノート

反応式

HRID 411737 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:12]=1[CH2:13]Br.[H-].[Na+]>CN(C)C=O>[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:12]=1[CH2:13][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 1264-HydroxybenzaldehydeHCID 24758Sodium hydrideHCID 301591-Bromomethyl-2,6-dichlorobenzene

生成物 1

HCID 7354664-[(2,6-dichlorobenzyl)oxy]benzaldehyde収率 107.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-hydroxybenzaldehyde (3.59 g, 24.39 mmol) and 2,6-dichlorobenzyl bromide (7.05 g, 29.39 mmol) in dimethylformamide (20 mL) at 0° C. was added 60% sodium hydride (1.176 g, 29.39 mmol). After stirring at ambient temperature for 16 h, the reaction was partitioned between ethyl acetate and water. The organic layer was washed with aqueous sodium chloride and dried (MgSO4). Purification by flash column chromatography (silica gel, hexane/ethyl acetate) yielded the title compound as an off-white solid (7.38 g, 89%).

後処理

  1. customthe reaction was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with aqueous sodium chloride
  3. dry with materialdried (MgSO4)
  4. customPurification by flash column chromatography (silica gel, hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-5d7a1c1838f54022afafa11675904a05
出典データセット
uspto-grants-2003_05
特許番号
US06559179B1

反応ノート

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