2-Bromopropane → Methyl 2-(4-isopropoxyphenyl)acetate

HRID 1852087

Reaktionsgleichung

Reaktionsgleichung von HRID 1852087
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.Br[CH:14]([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:14]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1)([CH3:16])[CH3:15]

Komponenten

5

Edukt 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Produkt 1

HCID 525538Methyl 2-(4-isopropoxyphenyl)acetateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methyl 2-(4-hydroxyphenyl)acetate (10 g, 60.2 mmol), 2-bromopropane (6.49 mL, 69.2 mmol), and potassium carbonate (8.32 g, 60.2 mmol) were heated to 50° C. in DMF (100 mL) for overnight. The reaction was filtered and the organic layer was concentrated under vacuum. The crude material was purified by silica gel chromatography using a gradient of 0-20% EtOAc/hexanes. The product fractions were collected and the solvent removed under vacuum to give methyl 2-(4-isopropoxyphenyl)acetate (10 g, 80% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.22-7.14 (m, 2H), 6.88-6.82 (m, 2H), 4.53 (spt, J=6.1 Hz, 1H), 3.70 (s, 3H), 3.57 (s, 2H), 1.34 (d, J=6.0 Hz, 6H).

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. concentrationthe organic layer was concentrated under vacuum
  3. customThe crude material was purified by silica gel chromatography
  4. customThe product fractions were collected
  5. customthe solvent removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-901c2da79ae248e6b47075d9e0b58102
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957203B2

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