3,4-Bis(benzyloxy)benzaldehyde → 3,4-Bis(benzyloxy)benzyl alcohol

HRID 403010

Reaktionsgleichung

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:12][OH:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

3,4-Dibenzyloxybenzaldehyde (27) (22.0 mmol) was suspended in 100 mL of anhydrous methanol and cooled to 0° C. under argon. Sodium borohydride (33.0 mmol) was added in portions to the suspension and stirred for 1 h at the same temperature. The resulting solution was then stirred at room temperature overnight. The reaction mixture was evaporated to dryness and the residue was dissolved in ice-water and neutralized with HCl. The solution was then extracted with chloroform and the organic layer was washed successively with water, 10% NaHCO3 solution in water and brine. The organic layer was dried over anhydrous Na2SO4, filtered and evaporated to dryness to provide pure 3,4-Dibenzyloxybenzyl alcohol (28) in 97.5% yield.

Aufarbeitung

stirringThe resulting solution was then stirred at room temperature overnight
customThe reaction mixture was evaporated to dryness
dissolutionthe residue was dissolved in ice-water and neutralized with HCl
extractionThe solution was then extracted with chloroform
washthe organic layer was washed successively with water, 10% NaHCO3 solution in water and brine
dry with materialThe organic layer was dried over anhydrous Na2SO4
filtrationfiltered
customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag: ord-17c46815fde54f19a6db355bcab2ae54
Quelldatensatz: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08742139B2

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