Water → 3-(Benzyloxy)-4-methoxybenzyl alcohol

HRID 541166

Reaktionsgleichung

Reaktionsgleichung von HRID 541166
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH2:12][OH:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[OH:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH2:12][OH:13]

Komponenten

5

Edukt 2

HCID 962WaterHCID 806713-Benzyloxy-4-methoxybenzaldehyde

Produkt 2

HCID 746223-(Benzyloxy)-4-methoxybenzyl alcoholHCID 780893-Hydroxy-4-methoxybenzyl alcohol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

121.1 mg (0.50 mmol) of 3-benzyloxy-4-methoxybenzaldehyde (7), 270 μL (15 mmol) of distilled water and stainless steel balls (50 pieces) were placed in the vessel of the planetary ball mill, which was then closed, and agitated by operating the planetary ball mill for 12 hours at 800 rpm (reversed every 30 minutes). After the lapse of 12 hours, 10 mL of ethyl acetate was added to the vessel of the ball mill to provide a solution containing the reaction mixture, which was then filtered with celite. The operation was repeated 5 times to provide a filtrate, which was then concentrated, thereby providing 74.0 mg (0.31 mmol) of 3-benzyloxy-4-methoxybenzyl alcohol (8) and 6.9 mg (0.05 mmol) of 3-hydroxy-4-methoxybenzyl alcohol (9). The yields were 61% and 9%, respectively. The reaction is expressed by the following scheme. 23.7 mg (0.10 mmol) of unreacted 3-benzyloxy-4-methoxybenzaldehyde (7) was recovered.

Aufarbeitung

  1. customwas then closed
  2. customfor 12 hours
  3. customto provide a solution
  4. additioncontaining the reaction mixture, which
  5. filtrationwas then filtered with celite
  6. customto provide a filtrate, which
  7. concentrationwas then concentrated

Quellen und Nachweise

ORD-Eintrag
ord-2e7f6a84271b4e71b532d9f211b0340c
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871980B2

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