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Ethylene Glycol → 2,2-Bis((benzyloxy)methyl)-1,3-dioxolane

HRID 31581
ノート
印刷プレビュー

反応式

HRID 31581 の反応式
[CH2:1]([O:8][CH2:9][C:10]([CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21](O)[CH2:22][OH:23].C(OCC)(OCC)OCC.C(=O)([O-])O.[Na+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>[CH2:1]([O:8][CH2:9][C:10]1([CH2:12][O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[O:23][CH2:22][CH2:21][O:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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 4

HCID 174Ethylene GlycolHCID 31214Ethyl orthoformateHCID 516892Sodium BicarbonateHCID 113915821,3-Bis(benzyloxy)propan-2-one

生成物 1

HCID 597925122,2-Bis((benzyloxy)methyl)-1,3-dioxolane収率 81.6%

試薬・触媒・溶媒 2

HCID 521998
p-Toluenesulfonic acid monohydrate
触媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

The 1,3-bis(benzyloxy)acetone (30 g, 111 mmol) obtained in the step (4a) was mixed with ethylene glycol (64 ml, 1,148 mmol) and triethyl orthoformate (19 ml, 114 mmol), and p-toluenesulfonic acid monohydrate (591 mg, 3.11 mmol). The mixture was stirred at 50° C. for 14 hours. To the mixture, a saturated aqueous solution of sodium hydrogen carbonate and ethyl acetate were added. The organic layer was washed with water and a saline solution, dried over anhydrous sodium sulfate, and concentrated. The obtained crude product was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate=1/0-4/1 gradient) and desired fractions were concentrated to obtain the title compound (28.46 g, yield: 81.6%) as a colorless oil.

後処理

  1. washThe organic layer was washed with water
  2. dry with materiala saline solution, dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe obtained crude product
  5. customwas purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate=1/0-4/1 gradient)
  6. concentrationdesired fractions were concentrated

出典と根拠

ORDレコード
ord-9a9bacf391a74083b5f0c32cbb89a655
出典データセット
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07425634B2

反応ノート

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