Methanol → 2,2-diethoxyethyl Benzoate

HRID 31710

反応式

HRID 31710 の反応式
N1C=CC=CC=1.[CH2:7]([O:9][CH:10]([O:13][CH2:14][CH3:15])[CH2:11][OH:12])[CH3:8].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CO>C(OCC)(=O)C.O>[C:16]([O:12][CH2:11][CH:10]([O:13][CH2:14][CH3:15])[O:9][CH2:7][CH3:8])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

7

反応物 4

HCID 887MethanolHCID 1049PyridineHCID 7412Benzoyl chlorideHCID 121292,2-Diethoxyethanol

生成物 1

HCID 118172582,2-diethoxyethyl Benzoate収率 96.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a pyridine (30 ml) solution of glycol aldehyde diethylacetal (19.8 g, 148 mmol), benzoyl chloride (51.7 ml, 444 mmol) was added dropwise at −20 to 30° C. The mixture was stirred at room temperature for 167 hours and 50 minutes. After methanol and water were added to the mixture, extraction with ethyl acetate was performed. The obtained organic layer was washed with a saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogencarbonate solution, and a saturated saline solution. After dried over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and purified by silica gel column chromatography (elution solvent: heptane, ethyl acetate/heptane=1/9). Thereafter, purification by silica gel column chromatography (elution solvent: heptane, ethyl acetate/heptane=1/100, 1/30, 1/10) was performed again to obtain the title compound (34 g, yield: 96.4%) as a light green oil.

後処理

  1. washThe obtained organic layer was washed with a saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogencarbonate solution
  2. dry with materialAfter dried over anhydrous magnesium sulfate
  3. concentrationthe mixture was concentrated under reduced pressure
  4. custompurified by silica gel column chromatography (elution solvent: heptane, ethyl acetate/heptane=1/9)
  5. customThereafter, purification
  6. washby silica gel column chromatography (elution solvent: heptane, ethyl acetate/heptane=1/100, 1/30, 1/10)

出典と根拠

ORDレコード
ord-b344b96185124106ab3614c124b56f56
出典データセット
uspto-grants-2008_09
特許番号
US07425634B2

関連ノート

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