Dimethylformamide → 1,1'-Biphenyl, 2,2'-bis(methoxymethoxy)-

HRID 859081

反応式

HRID 859081 の反応式
[H-].[Na+].CN(C=O)C.[C:8]1([OH:21])[C:9]([C:14]2[C:15]([OH:20])=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1.[CH3:22][O:23][CH2:24]Cl.C1[CH2:30][O:29][CH2:28]C1>>[CH3:22][O:23][CH2:24][O:21][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH2:28][O:29][CH3:30]

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 8028Tetrahydrofuran2 回HCID 15731(1,1'-Biphenyl)-2,2'-diolHCID 24758Sodium hydride

生成物 1

HCID 114713211,1'-Biphenyl, 2,2'-bis(methoxymethoxy)-収率 97%

実験手順

To a 250 mL of three-necked bottle was added NaH (content 50%, 3.5 g, 72 mmol), anhydrous THF (60 mL) and anhydrous DMF (20 mL), after the temperature was lowered to 0° C., a solution of biphenol (5.6 g, 30 mmol) in THF (15 mL) was added, stirred at this temperature for 10 minutes. Methoxymethyl chloride (6 mL, 78 mmol) was added dropwise, and the mixture was stirred for 8 h at room temperature, quenched by adding 100 mL of water, extracted with ethyl acetate (100 mL×3), the combined organic phase was washed with brine (60 mL×2), dried over MgSO4, after filtration, the solvent was removed to give a yellow oil. Purification through chromatography give 8 g (97% yield) of the product as a light yellow oil. 1HNMR (300 MHz, CDCl3) δ (ppm) 3.39 (s, 6H), 5.12 (s, 4H), 7.13 (m, 2H), 7.30–7.37 (m, 6H). Physical data of the compound was consistent with that reported in literature.

後処理

  1. customwas lowered to 0° C.
  2. stirringthe mixture was stirred for 8 h at room temperature
  3. customquenched
  4. additionby adding 100 mL of water
  5. extractionextracted with ethyl acetate (100 mL×3)
  6. washthe combined organic phase was washed with brine (60 mL×2)
  7. dry with materialdried over MgSO4
  8. filtrationafter filtration
  9. customthe solvent was removed
  10. customto give a yellow oil
  11. customPurification through chromatography

出典と根拠

ORDレコード
ord-d4e93b93b1a240b8be74ac423b42f8aa
出典データセット
uspto-grants-2006_12
特許番号
US07151070B2

関連ノート

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