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

HRID 31581
Notes
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Reaction equation

HRID 31581 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 521998
p-Toluenesulfonic acid monohydrate
Catalyst
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9a9bacf391a74083b5f0c32cbb89a655
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07425634B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes