Реакция #59886

Уравнение реакции

2-(hydroxymethyl)-1,3-propanediol

tetrahydro-4H-pyran-4-one

benzene

→

title compound

Выход 64.9%

1,5,9-trioxaspiro[5.5]undec-3-ylmethanol

Выход 64.9%

Растворители

triethylamine

Условия реакции

Обработка

1. 1
   Температураwas refluxed in a round bottom flask
2. 2
   Другоеequipped with a cooling tube
3. 3
   Концентрированиеthe mixture was concentrated
4. 4
   ДругоеThe residue was purified by silica gel column chromatography (silica gel: 200 g, elution solvent: heptane, heptane/ethyl acetate=1/1, 1/3)

Методика

A mixture of 2-(hydroxymethyl)-1,3-propanediol (3.3 g, 31.1 mmol), tetrahydro-4H-pyran-4-one (3.12 g, 31.2 mmol), p-toluenesulfonic acid monohydrate (268 mg, 1.41 mmol) and benzene (68.3 ml) was refluxed in a round bottom flask equipped with a cooling tube and Dean-Stark for 6 hours. After cooled to room temperature, triethylamine (1 ml) was added to the reaction mixture and the mixture was concentrated. The residue was purified by silica gel column chromatography (silica gel: 200 g, elution solvent: heptane, heptane/ethyl acetate=1/1, 1/3) to obtain the title compound (3.80 g, yield: 64.9%) as a colorless oil.

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