Sodium Carbonate → Phenyl 4-[2-(2-methoxyethoxy)ethoxy]benzoate

HRID 2377258노트

반응식

HRID 2377258 반응식
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[CH3:26][O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 87250PhenylparabenHCID 1235321-Bromo-3,6-dioxaheptane

생성물 1

HCID 69202991Phenyl 4-[2-(2-methoxyethoxy)ethoxy]benzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of phenyl 4-hydroxybenzoate (2.1 g, 9.8 mmol) in tetrahydrofuran (40 mL) was added a 60% suspension of sodium hydride in mineral oil (408 mg, 10.2 mmol) and the mixture was stirred at room temperature for about 30 minutes. Then 1-bromo-2-(2-methoxyethoxy)ethane (2.5 g, 13.7 mmol) was added and stirring was continued for about 5 days. The mixture was poured into saturated aqueous sodium carbonate and was extracted with ethyl acetate, the combined organic extracts were washed with saturated aqueous sodium carbonate, dried (Na2SO4), filtered, and concentrated under vacuum. The residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (10:1) as eluent to provide the desired product. 1H NMR (500 MHz, CDCl3) δ 3.40 (s, 3H), 3.60 (m, 2H), 3.76 (m, 2H), 3.92 (t, J=8 Hz, 2H), 4.22 (t, J=8 Hz, 2H), 7.00 (d, J=8 Hz, 2H), 7.22 (m, 3H), 7.42 (d, J=8 Hz, 2H), 8.17 (d, J=8 Hz, 2H).

후처리

  1. stirringstirring
  2. waitwas continued for about 5 days
  3. extractionwas extracted with ethyl acetate
  4. washthe combined organic extracts were washed with saturated aqueous sodium carbonate
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-ab33dc03484642cd942b6d262880b18b
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07468371B2

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