Benzyl Bromide → Methyl 3,5-bis(benzyloxy)benzoate

HRID 1757844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1757844
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([OH:11])[CH:5]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:5]=[C:6]([O:11][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=[C:8]([O:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:9]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 75076Methyl 3,5-Dihydroxybenzoate

Produkt 1

HCID 2733652Methyl 3,5-bis(benzyloxy)benzoateAusbeute 160,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 25.0 g (0.15 mol) of 3,5-dihydroxybenzoic acid methyl ester, 44 ml (0.37 mol) of benzyl bromide and 82 g (0.60 mol) of potassium carbonate in 300 ml of DMF was stirred and heated at 85° under argon for 45 hours. The cooled reaction mixture was filtered and the filtrate was concentrated at reduced pressure. The residue was treated with methylene chloride and the extract was filtered again to remove salts. Crystallization from methylene chloride-methanol gave 41.9 g (81% yield, mp 64°-66°) of 3,5-bis(phenylmethoxy)benzoic acid methyl ester.

Aufarbeitung

  1. temperatureheated at 85° under argon for 45 hours
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated at reduced pressure
  5. additionThe residue was treated with methylene chloride
  6. filtrationthe extract was filtered again
  7. customto remove salts
  8. customCrystallization from methylene chloride-methanol

Quellen und Nachweise

ORD-Eintrag
ord-85912af37a5e46089cb2f44eece6ed93
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05446189

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