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

HRID 1645632

反応式

HRID 1645632 の反応式
[CH2:1]([O:8][CH2:9][CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12](O)[CH2:13][OH:14].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH:10]1[O:14][CH2:13][CH2:12][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 108989(Phenylmethoxy)acetaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 138892432-((Benzyloxy)methyl)-1,3-dioxolane収率 77.5%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
140 °C

実験手順

A mixture of benzyloxyacetaldehyde (3 g, 20 mmol), ethylene glycol (1.23 ml, 22 mmol), p-toluenesulfonic acid monohydrate (344 mg, 1.8 mmol), and toluene (15 ml) was stirred at 140° C. for 2 hours and further stirred at 150° C. for 3 hours. After cooled on ice, a 2N aqueous sodium hydroxide solution and ethyl acetate were added to the reaction mixture. An organic layer was separated, washed with water (three times) and a saturated saline solution. The organic layer was dried over anhydrous sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 9/1 gradient). Desired fractions were concentrated to obtain the title compound (3.01 g, 77.5% yield) as a light yellow oil.

後処理

  1. stirringfurther stirred at 150° C. for 3 hours
  2. temperatureAfter cooled on ice
  3. customAn organic layer was separated
  4. washwashed with water (three times)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 9/1 gradient)
  8. concentrationDesired fractions were concentrated

出典と根拠

ORDレコード
ord-271710adb03d400f9f9013d417e8f419
出典データセット
uspto-grants-2012_02
特許番号
US08124780B2

関連ノート

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