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Benzaldehyde → [2,4-Bis(methoxymethoxy)-6-(2-methoxyethyl)phenyl]phenylmethanol

HRID 499864
ノート
印刷プレビュー

反応式

HRID 499864 の反応式
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6](Br)=[C:7]([CH2:15][CH2:16][O:17][CH3:18])[CH:8]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:10]=1.C([Li])CCC.CCCCCC.[CH:31](=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:8]=[C:7]([CH2:15][CH2:16][O:17][CH3:18])[C:6]=1[CH:31]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[OH:38]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 240BenzaldehydeHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 231164713,5-Bis(methoxymethoxy)-2-bromo-1-(2-methoxyethyl)benzeneHCID 178418339Butyllithium

生成物 1

HCID 23116486[2,4-Bis(methoxymethoxy)-6-(2-methoxyethyl)phenyl]phenylmethanol収率 53%

試薬・触媒・溶媒

1
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

3,5-Bis(methoxymethoxy)-2-bromo-1-(2-methoxyethyl)-benzene (5.3 g, 16 mmol) obtained in Example 1, Step 4 was dissolved in tetrahydrofuran (0.10 L). After the solution was cooled to −78° C., a 1.6 mol/L solution of n-butyllithium in hexane (30 mL, 48 mmol) was added thereto, followed by stirring for 5 minutes. Benzaldehyde (6.4 mL, 62 mmol) was added to the reaction mixture, followed by stirring for 1 hour. To the reaction mixture was added a saturated aqueous solution of ammonium chloride (30 mL), and the mixture was extracted with ethyl acetate (0.30 L). The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-1/2) to obtain [2,4-bis(methoxymethoxy)-6-(2-methoxyethyl)phenyl]phenyl-methanol (3.0 g, 53%). Then, [2,4-bis(methoxymethoxy)-6-(2-methoxyethyl)phenyl]phenylmethanol (3.0 g, 8.4 mmol) was dissolved in dichloromethane (50 mL), and Molecular Sieves 4 (7.9 g) and pyridinium dichromate (7.9 g, 21 mmol) were added thereto, followed by stirring at room temperature for 5 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-1/2) to obtain 2,4-bis(methoxymethoxy)-6-(2-methoxyethyl)phenyl=phenyl=ketone (2.9 g, 96%).

後処理

  1. stirringby stirring for 1 hour
  2. extractionthe mixture was extracted with ethyl acetate (0.30 L)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-1/2)

出典と根拠

ORDレコード
ord-a10ea36789c3416e879c24a163ff6b87
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07767693B2

反応ノート

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