Benzyl Bromide → Benzyl 2-(3-(benzyloxy)phenyl)acetate

HRID 1180181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180181
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[C:19]1([CH2:18][O:1][C:2]2[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:8][C:4]3[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=3)=[O:10])[CH:5]=[CH:6][CH:7]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 121223'-Hydroxyphenylacetic acid

Produkt 1

HCID 15470856Benzyl 2-(3-(benzyloxy)phenyl)acetateAusbeute 198,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-hydroxyphenyl acetic acid (5.0 g, 0.03 mol) in DMF (25 ml) was added potassium carbonate (12.4 g, 0.09 mol). The reaction was allowed to stir for twenty minutes at which time benzyl bromide (8.9 ml, 0.075 mol) was added to the flask. The reaction was allowed to stir overnight. Solvent was removed. The reaction was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated to yield the title compound (9.9 g, 99% yield): ES-MS (m/z) 243 [M+H]+.

Aufarbeitung

  1. additionwas added to the flask
  2. customSolvent was removed
  3. additionThe reaction was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c022eaba1cfe4f60bd1f66f6fa3c3cf6
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279489B2

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