Benzene → HCID 59792598, compound

A mixture of 2-(hydroxymethyl)-1,3-propanediol (5.58 g, 52.6 mmol), cyclobutanone (3.69 g, 52.6 mmol), p-toluenesulfonic acid monohydrate (550 mg, 2.89 mmol) and benzene (92.9 ml) was refluxed in a round-bottom flask equipped with a cooling tube and Dean-Stark for 8 hours and 35 minutes. After the reaction mixture was 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: 300 g, elution solvent: heptane, heptane/ethyl acetate=1/1). The fractions containing the title compound were collected with ethyl acetate and concentrated. The residue was dissolved in diethyl ether and then the mixture was concentrated to obtain the title compound (6.08 g, yield: 73.1%) as a pale yellow oil.

1. temperaturewas refluxed in a round-bottom flask
2. customequipped with a cooling tube
3. custom35 minutes
4. concentrationthe mixture was concentrated
5. customThe residue was purified by silica gel column chromatography (silica gel: 300 g, elution solvent: heptane, heptane/ethyl acetate=1/1)
6. additionThe fractions containing the title compound
7. customwere collected with ethyl acetate
8. concentrationconcentrated
9. dissolutionThe residue was dissolved in diethyl ether
10. concentrationthe mixture was concentrated

ORD record

ord-10d857c5642d4841825bb81d87fb3f52

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08124780B2