Benzyl Bromide → Benzyl 2-Benzylacrylate

HRID 36375

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HRID 36375 반응식
[CH2:1]=[C:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(OCC)(=O)C>CN(C)C=O>[CH2:1]=[C:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:5][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:4]

참가 물질

6

반응물 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 3035712-Benzylacrylic Acid

생성물 1

HCID 10912012Benzyl 2-Benzylacrylate수율 60.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

The title acid of Step 9 (5.2 g, 30 mmol) was dissolved in dimethylformamide (25 mL) and cooled to 0° C. To this solution potassium carbonate (5.7 g, 41.48 mmol) was added followed by benzyl bromide (5.7 g, 29.7 mmol). The mixture was stirred at room temperature overnight. The mixture was filtered and the filtrate was diluted with ethyl acetate, washed with 3 times of water, brine. The solution was dried (Na2SO4) and evaporated. The residue was purified by flash chromotography on silica gel, eluting with 90:10 heptane:ethyl acetate to give the pure title compound as colorless oil (4.5 g, 60% yield). 1H NMR: 300 MHz spectrum consistent with proposed structure. Anal: calcd. for C17H16O2 : C, 80.93; H, 6.39. Found: C, 80.69; H, 6.47.

후처리

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed with 3 times of water, brine
  4. dry with materialThe solution was dried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by flash chromotography on silica gel
  7. washeluting with 90:10 heptane

출처 및 근거

ORD 기록
ord-2d79bf1e031f404cbd4495a86c976c85
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05414018

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