Sodium borohydride → 4-(3-Chloropropoxy)-3-hydroxy-alpha-methylbenzenemethanol

HRID 233852

Reaktionsgleichung

[BH4-].[Na+].[Cl:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][C:9]=1[OH:17]>C(O)C.O1CCCC1>[Cl:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:15])[OH:16])=[CH:10][C:9]=1[OH:17]

Komponenten

Reaktionsbedingungen

Temperatur: 10 °C

Versuchsvorschrift

To a flask charged with sodium borohydride (1.5 g, 39.4 mmol) under nitrogen and chilled to 10° C. was added, slowly, a solution of 1-[4-(3-chloropropoxy)-3-hydroxyphenyl]ethanone (6.0 g, 26.2 mmol) dissolved in ethanol-tetrahydrofuran (120 ml, 2:1). After total addition, the ice bath was removed and the reaction was stirred at ambient temperature for 3 hours. An additional amount of sodium borohydride (0.2 g, 5.3 mmol) was carefully added. After stirring at ambient temperature for one hour, the solvent was removed in vacuo. The resultant solid residue was diluted with water (100 ml) and left overnight. The product was isolated by vacuum filtration yielding 3.8 g. Two consecutive recrystallizations from toluene provided 3.3 g (55%) of 4-(3-chloropropoxy)-3-hydroxy-α-methylbenzene methanol as a light brown solid, m.p.=107°-109° C.

Aufarbeitung

additionwas added
additionAfter total addition
customthe ice bath was removed
stirringAfter stirring at ambient temperature for one hour
customthe solvent was removed in vacuo
additionThe resultant solid residue was diluted with water (100 ml)
waitleft overnight
customThe product was isolated by vacuum filtration
customyielding 3.8 g
customTwo consecutive recrystallizations from toluene

Quellen und Nachweise

ORD-Eintrag: ord-d6cd5509a98541a4a786b6e9688f9815
Quelldatensatz: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05593995

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