2-Methyl-2-phenyl-1,3-dioxolane → 4-Ethyl-2-phenyloctan-2-ol

HRID 1516952

Reaktionsgleichung

Reaktionsgleichung von HRID 1516952
[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:6]CCO1.S([O-])(OCCCCCCCCCCCC)(=O)=O.[Na+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:43]([CH:45]([CH2:49][CH2:50][CH2:51][CH3:52])[CH2:46][Mg]Br)[CH3:44]>O.C(OCC)C>[CH2:43]([CH:45]([CH2:49][CH2:50][CH2:51][CH3:52])[CH2:46][C:2]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)([OH:6])[CH3:1])[CH3:44]

Komponenten

7

Edukt 4

HCID 1380062-Methyl-2-phenyl-1,3-dioxolaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 3423265Sodium Lauryl SulfateHCID 178443576HCID 178443576, Verbindung

Produkt 1

HCID 634066254-Ethyl-2-phenyloctan-2-olAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

2-Methyl-2-phenyl-1,3-dioxolane (0.25 g, 1.5 mmol), sodium dodecyl sulfate (0.1 g, 0.35 mmol) and a stir bar were added to the inside of a PDMS thimble. p-Toluene sulfonic acid monohydrate (72.4 mg, 0.38 mmol) dissolved in 2 mL water was added to the inside of the PDMS thimble followed by 1 mL of hexanes. The reaction was stirred at 25° C. for 4 hours. Hexanes (2.5 mL) was added to the outside of the PDMS thimble followed by 12 mL of 1 M 2-ethylhexyl-magnesiumbromide (2.6 g, 12 mmol). The reaction was stirred for an additional 12 hours after which 5 mL water was added. The PDMS thimble was swelled with 20 mL hexanes and 2×20 mL diethyl ether. The organics were combined and dried over MgSO4. The product was purified by column chromatography, eluting with 100% hexanes to yield a colorless oil (0.28 g, 80% yield). 1H NMR (CDCl3): δ 0.68-0.86 (m, 6H), 1.08-1.29 (m, 9H), 1.57 (s, 3H), 1.63 (s, 1H), 1.70-1.75 (m, 2H), 7.19-7.46 (m, 5H). 13C NMR (CDCl3): δ 10.43, 10.49, 14.00, 14.05, 22.86, 22.95, 26.95, 27.12, 28.48, 28.61, 30.45, 30.72, 33.82, 34.04, 34.62, 34.68, 47.99, 48.01, 75.07, 75.09, 124.82. 124.84, 126.27, 126.31, 127.88, 148.32, 148.38. HRMS: Calculated for C16H26O: 234.1984.

Aufarbeitung

  1. additionwas added
  2. dry with materialdried over MgSO4
  3. customThe product was purified by column chromatography
  4. washeluting with 100% hexanes

Quellen und Nachweise

ORD-Eintrag
ord-1cd74bb2ac554aff849bdb1f7a2fe3f6
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227635B2

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