Benzyl Bromide → Methyl 3-(benzyloxy)-5-hydroxy-4-methylbenzoate

HRID 1025195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1025195
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:13])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:13])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 11458051Methyl 3,5-dihydroxy-4-methylbenzoate

Produkt 1

HCID 67211670Methyl 3-(benzyloxy)-5-hydroxy-4-methylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methyl 3,5-dihydroxy-4-methylbenzoate (3.5 g, 19.22 mmol, 1.0 eq) was dissolved in 300 ml of DMF. To this solution potassium carbonate (2.52 g, 18.26 mmol, 0.95 eq) was added. To this stirred suspension, benzyl bromide (3.12 g, 18.26 mmol, 0.95 eq) (diluted with 50 ml of DMF) was added dropwise over a period of 3 h. The solution was stirred overnight at ambient temperature. Then DMF was evaporated under reduced pressure. The residue was washed with water and the product was extracted thrice with DCM. The combined DCM layers was dried over sodium sulphate and evaporated under vacuum. The required product was purified by silica gel (240-400) column chromatography using 10% ethyl acetate/hexane as the eluent. Yield: 1.6 g (30%). 1H NMR (400 MHz, DMSO-d6): δ 2.07 (s, 3H), 3.81 (s, 3H), 5.14 (s, 2H), 7.08 (s, 1H), 7.14 (s, 1H), 7.33-7.35 (d, 1H, J=7.04 Hz), 7.39-7.42 (t, 2H, J=7.40 Hz), 7.46-7.48 (d, 2H, J=7.48 Hz), 9.78 (s, 1H).

Aufarbeitung

  1. customThen DMF was evaporated under reduced pressure
  2. washThe residue was washed with water
  3. extractionthe product was extracted thrice with DCM
  4. dry with materialThe combined DCM layers was dried over sodium sulphate
  5. customevaporated under vacuum
  6. customThe required product was purified by silica gel (240-400) column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7bb163c0b2ea4f6d8bd86f997c674305
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722688B2

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