Benzene → 1,5,9-Trioxaspiro[5.5]undec-3-ylmethanol

HRID 31608

Reaktionsgleichung

Reaktionsgleichung von HRID 31608
[OH:1][CH2:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5].[O:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1.C1C=CC=CC=1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>[O:1]1[C:11]2([CH2:12][CH2:13][O:8][CH2:9][CH2:10]2)[O:5][CH2:4][CH:3]([CH2:6][OH:7])[CH2:2]1

Komponenten

6

Edukt 3

HCID 241BenzeneHCID 78432TrimethylolmethaneHCID 121599Tetrahydro-4H-pyran-4-one

Produkt 1

HCID 597924841,5,9-Trioxaspiro[5.5]undec-3-ylmethanolAusbeute 64,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-c133892f470943a9b26913e71107a107
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425634B2

Verknüpfte Notizen

Wird geladen…