Borane → (4-(Phenoxymethyl)phenyl)methanol

HRID 1827961

Reaktionsgleichung

Reaktionsgleichung von HRID 1827961
[O:1]([CH2:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B>O1CCCC1>[O:1]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][OH:14])=[CH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 6331BoraneHCID 7372674-(Phenoxymethyl)benzoic acid

Produkt 1

HCID 11333367(4-(Phenoxymethyl)phenyl)methanolAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-Phenoxymethylbenzoic acid 3 (3.424 g, 15.0 mmol) was dissolved in tetrahydrofuran (THF) (50 ml) and cooled to 0° C. A solution of borane in THF (33 ml, 33.0 mmol) was added dropwise at 0° C. The solution was then allowed to warm to room temperature and stir overnight. The mixture was then quenched with water, aqueous NaOH was added, and stirred for 30 min. The solution was then acidified with dilute HCl and extracted. The extracts were dried, concentrated, and purified by chromatography to give about 2.9 g of crystalline 4-phenoxymethylphenylmethanol 4.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. customThe mixture was then quenched with water, aqueous NaOH
  3. additionwas added
  4. stirringstirred for 30 min
  5. extractionextracted
  6. customThe extracts were dried
  7. concentrationconcentrated
  8. custompurified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2ac7a51c2841413a803e6f8ff2583aa5
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07056903B2

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