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

HRID 31581
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HRID 31581 반응식
[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
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참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 521998
p-Toluenesulfonic acid monohydrate
촉매
HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9a9bacf391a74083b5f0c32cbb89a655
출처 데이터셋
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07425634B2

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