Dimethyl Sulfoxide → 4-Benzyloxy-3-hydroxybenzaldehyde

HRID 356932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 356932
[OH-].[Na+].CS(C)=O.[OH:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[OH:16])[CH:11]=[O:12].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[CH2:17]([O:16][C:15]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][C:8]=1[OH:7])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 7498Benzyl BromideHCID 87683,4-DihydroxybenzaldehydeHCID 14798Sodium Hydroxide

Produkt 1

HCID 5613694-Benzyloxy-3-hydroxybenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A stirred solution of sodium hydroxide (16.8 g) in water (32 mL) at 20° C. is treated with dimethyl sulfoxide (560 mL). It is then treated with 3,4-dihydroxy-benzaldehyde (56.9 g), portionwise during 5 minutes, while keeping the temperature at 20° C. It is then treated with benzyl bromide (49.7 mL), portionwise, at 20° C. The solution is then heated at 80° C. for 6 hours and then allowed to stand at room temperature overnight. After dilution with ice-water (2240 mL) the solution is extracted with diethyl ether (1×1000 mL, 2×250 mL). The combined ether extracts are washed with water, dried over magnesium sulfate and concentrated, to give an oily solid, which is recrystallized from a mixture of ethyl acetate and isopropanol, to give 4-benzyloxy-3-hydroxybenzaldehyde (60.9 g), in the form of pale yellow crystals, m.p. 118°-120° C.

Aufarbeitung

  1. customat 20° C
  2. customat 20° C
  3. extractionAfter dilution with ice-water (2240 mL) the solution is extracted with diethyl ether (1×1000 mL, 2×250 mL)
  4. washThe combined ether extracts are washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give an oily solid, which
  8. customis recrystallized from a mixture of ethyl acetate and isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-cb3aa7fa6baa43a3aba56ef9350cfa9a
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840724

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