Benzyl Bromide → Benzyl 3-(benzyloxy)-4-methoxybenzoate

HRID 1808501

Reaktionsgleichung

Reaktionsgleichung von HRID 1808501
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:6]([O:7][CH3:8])=[C:4]([OH:5])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C.[Cl-].[Na+].O>[CH2:19]([O:5][C:4]1[CH:3]=[C:2]([CH:10]=[CH:9][C:6]=1[O:7][CH3:8])[C:1]([O:12][CH2:1][C:2]1[CH:10]=[CH:9][CH:6]=[CH:4][CH:3]=1)=[O:11])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl Bromide2×HCID 11430Potassium CarbonateHCID 12575Isovanillic Acid

Produkt 1

HCID 22070447Benzyl 3-(benzyloxy)-4-methoxybenzoateAusbeute 180,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To an ice cold mixture of isovanillic acid 1 (4.3 g, 25.5 mmol) and K2CO3 (10.5 g, 0.152 mol) in anhydrous DMF (40 mL) was added benzyl bromide (8.7 g, 6.05 mL, 51.1 mmol). The resulting reaction mixture stirred at RT overnight. An additional aliquot of benzyl bromide was added (1.0 ml) and stirring was continued for 1.5 h. The reaction mixture was poured into brine (100 mL) and the solid was collected via filtration, washed with water and dried under high vacuum to give benzyl 3-(benzyloxy)-4-methoxybenzoate as a white solid (7.99 g, 23.0 mmol, 90%).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. stirringstirring
  3. waitwas continued for 1.5 h
  4. filtrationthe solid was collected via filtration
  5. washwashed with water
  6. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-52d001bf655849ca8a7feb9871c9a7d6
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357693B2

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