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

HRID 2377258ノート

反応式

HRID 2377258 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ab33dc03484642cd942b6d262880b18b
出典データセット
uspto-grants-2008_12
特許番号
US07468371B2

反応ノート

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