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

HRID 31687

反応式

HRID 31687 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-3cf244367dc94f98812ae6228bd6bf02
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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