Water → Ethyl 2-(benzyloxy)benzoate

HRID 38639

반응식

HRID 38639 반응식
[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CC#N>[CH2:19]([O:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 8365Ethyl SalicylateHCID 11430Potassium Carbonate

생성물 1

HCID 345928Ethyl 2-(benzyloxy)benzoate수율 94.71%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 68 (5.8 g, 34.9 mmol) in CH3CN (150 ml) was added K2CO3 (10.6 g, 76.8 mmol). The mixture was added benzyl bromide (6.57 g, 38.39 mmol) and refluxed for 8 h under N2 atmosphere. The reaction mixture was cooled to 25° and poured into H2O (500 ml), and then extracted with CH2Cl2. The organic layer was washed with H2O, dried over MgSO4 and evaporated. The crude products were purified by distillation to give 73 as colorless liquid. (8.5 g, 33.2 mmol). Yield: 94.71%; MS (EI, 70 eV): m/z 256.3 (M+); 1H-NMR (CDCl3, 200 MHz): δ 1.33=(t, J=7.2 Hz, 3H), 4.35 (q, =7.2, 7.0 Hz, 2H), 5.15 (s, 2H), 7.00 (d, =8.0 Hz, 2H), 7.32-7.45 (m, 5H), 7.49 (d, J=8.2 Hz, 1H), 7.82 (dd, J=8.2, 1.8 Hz, 1H); 13C-NMR (CDCl3, 50 MHz) δ: 166.60, 158.01, 136.77, 133.25, 131.69, 128.49, 127.80, 126.99, 121.20, 120.56, 113.75, 70.57, 60.93, 14.29; Anal. Calcd for C16H16O3: C, 74.98; H, 6.29.

후처리

  1. temperaturerefluxed for 8 h under N2 atmosphere
  2. temperatureThe reaction mixture was cooled to 25°
  3. extractionextracted with CH2Cl2
  4. washThe organic layer was washed with H2O
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. distillationThe crude products were purified by distillation

출처 및 근거

ORD 기록
ord-eb760ee673ac4bd98bb759caad1f3ae1
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524740B2

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