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

HRID 1019099노트

반응식

HRID 1019099 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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 an off-white solid (7.38 g, 89%). MS(ES) m/e 281.0 [M+H]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-8abf35b5f2624c83aede9bb3a8a9c8da
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06486192B1

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