4-Bromoanisole → 1-(5-Hydroxy-2-methoxyphenyl)-1-(4-methoxy-phenyl)-methanol

HRID 1761620

Reaktionsgleichung

Reaktionsgleichung von HRID 1761620
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Mg].[OH:11][C:12]1[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[C:16]([CH:19]=1)[CH:17]=[O:18].[Cl-].[NH4+]>O1CCCC1>[OH:11][C:12]1[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[C:16]([CH:17]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)[OH:18])[CH:19]=1

Komponenten

6

Edukt 4

HCID 77304-BromoanisoleHCID 25517Ammonium ChlorideHCID 3583415-Hydroxy-2-MethoxybenzaldehydeHCID 5462224Magnesium

Produkt 1

HCID 150239551-(5-Hydroxy-2-methoxyphenyl)-1-(4-methoxy-phenyl)-methanolAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To the Grignard reagent prepared from 4-bromoanisole (286 g) and magnesium turnings (38.5 g) in dry tetrahydrofuran (480 ml) was added, dropwise, with vigorous stirring, a solution of 5-hydroxy-2-methoxybenzaldehyde (100 g) in dry tetrahydrofuran (1 liter). The mixture was heated on a steam bath for 3 hours, cooled and decomposed with saturated ammonium chloride solution. The organic layer was removed and the aqueous extracted with ethyl acetate (twice). The combined organics were washed with water, dried with anhydrous magnesium sulphate and evaporated to dryness. The residue was stirred with water (4 liters), and the buff coloured solid collected and dried to give crude 1-(5-hydroxy-2-methoxyphenyl)-1-(4-methoxy- phenyl)-methanol (170 g, 99%), m.p. 62°-68°. This carbinol (85 g) was dissolved in ethanol (700 ml) and 10% palladium on charcoal (10 g) added. The mixture was hydrogenated in a Parr apparatus at 45° until hydrogen uptake ceased. The mixture was filtered, the filtrate evaporated to dryness and the residue filtered through a column containing silica gel, eluting with dichloromethane, to give 2,4'-dimethoxy-5-hydroxydiphenylmethane (46 g, 58%), m.p. 56°-58° (from petroleum spirit (60°-80°)).

Aufarbeitung

  1. additionwas added
  2. temperatureThe mixture was heated on a steam bath for 3 hours
  3. temperaturecooled
  4. customThe organic layer was removed
  5. extractionthe aqueous extracted with ethyl acetate (twice)
  6. washThe combined organics were washed with water
  7. dry with materialdried with anhydrous magnesium sulphate
  8. customevaporated to dryness
  9. customcollected
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6e72c25ae60642138ecfbb592a8b85e0
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04826876

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