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Benzene → 5-Benzyloxy-2-(3-methylphenyl)-1,3-dioxane

HRID 1678998
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1678998
[H-].[Na+].C1C=CC=CC=1.[OH:9][CH:10]1[CH2:15][O:14][CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=2)[O:12][CH2:11]1.[CH2:23](Cl)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1(C)C(C)=CC=CC=1>[CH2:23]([O:9][CH:10]1[CH2:11][O:12][CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=2)[O:14][CH2:15]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
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Komponenten

6

Edukt 4

HCID 241BenzeneHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 203649382-(3-Methylphenyl)-1,3-dioxan-5-ol

Produkt 1

HCID 203648845-Benzyloxy-2-(3-methylphenyl)-1,3-dioxaneAusbeute 91,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237
O-Xylene
Lösungsmittel

Versuchsvorschrift

A slurry of sodium hydride (2.1 g. 0.08 mole in 100 ml of xylene and 100 ml of benzene was stirred at ambient temperature while 5-hydroxy-2-(3-methylphenyl)-1,3-dioxane (15.9 g, 0.08 mole) was added dropwise during 1 hour. Stirring was continued for one hour and to the mixture was added benzyl chloride (10.4 g, 0.08 mole) during 0.5 hour. This mixture was heated under reflux for 22 hours, cooled, filtered and the filtrate washed with water (2 × 250 ml). The washed solution was dried over magnesium sulfate and concentrated under reduced pressure to give 20.9 g of oil which distilled at 2 × 10-4 mm. to give three fractions distilling respectively at 102°-133° C (cut 1); 133°-141° C (cut 2); and 141° C (cut 3). Analysis of the various cuts indicated that cut 3 was essentially pure cis-5 -benzyloxy-2-(3-methylphenyl)-1,3-dioxane, 2.1 g, m.p. 68°-70° C and this cut was used in further studies.

Aufarbeitung

  1. additionwas added dropwise during 1 hour
  2. temperatureThis mixture was heated
  3. temperatureunder reflux for 22 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. washthe filtrate washed with water (2 × 250 ml)
  7. dry with materialThe washed solution was dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d6cb5460598b44559658d2b8eab82672
Quelldatensatz
uspto-grants-1978_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04077982

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