Allyl bromide → 2-Allyloxy4-(benzyloxy)benzaldehyde

HRID 49246

반응식

HRID 49246 반응식
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].[CH2:20](Br)[CH:21]=[CH2:22]>CN(C)C=O>[CH2:22]([O:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[CH:21]=[CH2:20]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 5612354-Benzyloxy-2-hydroxybenzaldehyde

생성물 1

HCID 185460182-Allyloxy4-(benzyloxy)benzaldehyde수율 100%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

A solution of 45.8 g (0.20 mole) 2-hydroxy-4-(benzyloxy)benzaldehyde in 250 mL of dimethylformamide was added dropwise over 1 hour to a slurry of 10.6 g (0.26 mole) of 60% sodium hydride/mineral oil dispersion in 100 mL of dimethylformamide. The mixture was stirred under nitrogen for 1 hour at room temperature, and then 28 mL (0.33 mole) of allyl bromide in 30 mL of dimethylformamide was added. The reaction was heated at 60° C. for 4 hours under nitrogen. The solvent was then removed in vacuum and replaced with 500 mL of ethyl acetate. This solution was washed with 500 mL portions of 2 N aqueous HCl, saturated aqueous sodium bicarbonate and saturated brine, dried over sodium sulfate, filtered and concentrated in vacuum to give 53.6 g (100%) of the title compounds as a pale yellow solid. 1H-NMR (d6-DMSO): singlet 10.2 δ (1H); doublet of doublets 7.65 δ (1H); multiplet 7.40 δ (5H); doublet 6.80 δ (1H); doublet of doublets 6.75 δ (1H); multiplet 6.05 δ (1H); doublet of doublets 5.45 δ (1H); doublet of doublets 5.30 δ (1H); singlet 5.20 δ (2H); multiplet 4.70 δ (2H).

후처리

  1. temperatureThe reaction was heated at 60° C. for 4 hours under nitrogen
  2. customThe solvent was then removed in vacuum
  3. washThis solution was washed with 500 mL portions of 2 N aqueous HCl, saturated aqueous sodium bicarbonate and saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum

출처 및 근거

ORD 기록
ord-1922877ac3564494b01a980a8512965a
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706736B2

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