Hydrochloric Acid → (2-phenylcyclopropyl)methanol

HRID 1602570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1602570
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C@@H:13]2[CH2:15][C@H:14]2[C:16](O)=[O:17])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.Cl>O1CCCC1>[OH:17][CH2:16][C@@H:14]1[CH2:15][C@H:13]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 237413trans-2-Phenylcyclopropanecarboxylic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 1561175(2-phenylcyclopropyl)methanolAusbeute 103,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

152 mg of lithium aluminium hydride suspended in 10 ml of tetrahydrofuran was mixed with 324 mg of trans-2-phenylcyclopropane-1-carboxylic acid under cooling with ice and stirred at the same temperature for 30 minutes and then at room temperature for 2 hours. Water was gradually added to the reaction solution and then 1N hydrochloric acid was gradually added. The reaction solution was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=3/1→2/1] to give 307 mg of trans-l-(hydroxymethyl)-2-phenylcyclopropane as a colorless oily substance.

Aufarbeitung

  1. temperatureunder cooling with ice
  2. waitat room temperature for 2 hours
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationThe desiccant was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=3/1→2/1]

Quellen und Nachweise

ORD-Eintrag
ord-f096ecb36bc648428e9d36356d5ed396
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05981573

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