2-Methyl-2-phenyl-1,3-dioxolane → 1-Phenylethanol

HRID 1516951

Reaktionsgleichung

Reaktionsgleichung von HRID 1516951
[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)OCC[O:3]1.S([O-])(OCCCCCCCCCCCC)(=O)=O.[Na+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O.C(OCC)C>[C:7]1([CH:2]([OH:3])[CH3:1])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

7

Edukt 4

HCID 1380062-Methyl-2-phenyl-1,3-dioxolaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 3423265Sodium Lauryl SulfateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 74091-PhenylethanolAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

2-Methyl-2-phenyl-1,3-dioxolane (0.5 g, 3 mmol), sodium dodecyl sulfate (0.2 g, 0.7 mmol) and a stir bar were added to the inside of a PDMS thimble. p-Toluene sulfonic acid monohydrate (0.145 g, 0.8 mmol) was dissolved in 4 mL water and added to the inside of the PDMS thimble followed by 2 mL of hexanes. LiAlH4 (0.145 g, 3.8 mmol) was added to the outside of the PDMS thimble with 5 mL hexanes. The reaction was stirred at 25° C. for 19 hours. Water (5 mL) 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 1:4 ethyl acetate:hexanes to yield a colorless liquid (0.33 g, 89% yield). 1H NMR (CDCl3): δ 1.44 (d, J=6.9 Hz, 3H), 2.42 (s, 1H), 4.81 (q, J=6.9 Hz, 1H), 7.22-7.33 (m, 5H). 13C NMR (CDCl3): δ 25.05, 70.22, 125.31, 127.32, 128.37, 145.74.

Aufarbeitung

  1. dry with materialdried over MgSO4
  2. customThe product was purified by column chromatography
  3. washeluting with 1:4 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-01d236b5d68746079ef043d2a7701bd4
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227635B2

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