Benzyl Bromide → 2-benzyloxy-3-methylbenzaldehyde

HRID 1422315노트

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HRID 1422315 반응식
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].[H][H].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O.O>[CH2:15]([O:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

7

반응물 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 5227773-MethylsalicylaldehydeHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 110641372-benzyloxy-3-methylbenzaldehyde수율 91%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

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온도
20 °C

실험 절차

A solution of 2-hydroxy-3-methylbenzaldehyde 20.0 g (147 mmol) prepared by the above 1-(1) in dimethylformamide (DMF) (100 ml) was added to the suspension of sodium hydride 6.5 g (163 mmol) with purity 60% and DMF (40 ml) under ice-cooling. After completion of emission of hydrogen gas, benzyl bromide 25.0 g (147 mmol) was dropped to it in a ice bath. The reaction mixture was stirred for 4 hours at 20° C. After the disappearance of the raw material, water was added to the reaction mixture and it was extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed in vacuo and the residue was purified by silica gel chromatography (n-hexane-ethyl acetate) to give 2-benzyloxy-3-methylbenzaldehyde 29.9 g (yield: 91%).

후처리

  1. temperaturecooling
  2. extractionwas extracted with methylene chloride
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customthe residue was purified by silica gel chromatography (n-hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-2746587cf32144be97be7a78c86bf818
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06080895

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