Trimethylolpropane → 1,3-Dioxane-5-methanol, 5-ethyl-2,2-dimethyl-

HRID 931692

Reaktionsgleichung

Reaktionsgleichung von HRID 931692
[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][CH3:5])[OH:2].CO[CH:12](OC)[CH3:13].[CH2:16](N(CC)CC)C>O1CCCC1.[NH4+].[NH4+].[O-][Mo]([O-])(=O)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:4]([C:3]1([CH2:8][OH:9])[CH2:6][O:7][C:12]([CH3:13])([CH3:16])[O:2][CH2:1]1)[CH3:5]

Komponenten

7

Edukt 3

HCID 6510TrimethylolpropaneHCID 8471TriethylamineHCID 107951,1-Dimethoxyethane

Produkt 1

HCID 118161521,3-Dioxane-5-methanol, 5-ethyl-2,2-dimethyl-Ausbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 61578Diammonium molybdateKatalysatorHCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Trimethylolpropane (10.0 g; 74.6 mmol), 2,2-dimethoxyethane (9.01 g; 86.5 mmol) and p-toluenesulfonic acid monohydrate (0.369 g; 1.94 mmol) were dissolved in tetrahydrofuran (125 mL). The clear solution was stirred at ambient temperature for 24 h. TLC (stained with ammonium molybdate) confirmed near quantitative conversion of the starting triol. The reaction was neutralised with triethylamine (10 mL) and all volatiles were removed in vacuo. Colourless oily residue was passed through a silicagel column (eluent ethyl acetate/cyclohexane 1:1). The eluent was evaporated to provide (5-ethyl-2,2-dimethyl-1,3-dioxan-5-yl)methanol (12.34 g; 95% yield) as a colourless oil.

Aufarbeitung

  1. customall volatiles were removed in vacuo
  2. customThe eluent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-36b3516933c442f9b5823fb96a670468
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296835B2

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