Potassium Carbonate → 3-Hydroxy-5-(2-methyl-allyloxy)-benzoic acid methyl ester

Reaktionsgleichung

[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([CH3:23])=[CH2:22]>>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:3]=[C:2]([O:1][CH2:22][C:21]([CH3:23])=[CH2:20])[CH:11]=[C:10]([OH:12])[CH:9]=1

Komponenten

Edukt 3

HCID 11430Potassium Carbonate

HCID 75076Methyl 3,5-Dihydroxybenzoate

HCID 3577853-Bromo-2-methyl-1-propene

Produkt 1

HCID 595599323-Hydroxy-5-(2-methyl-allyloxy)-benzoic acid methyl ester

Versuchsvorschrift

The title compound was prepared in a similar manner as described for Intermediate 1a, from methyl 3,5-dihydroxybenzoate (15.0 g, 89.2 mmol), potassium carbonate (24.7 g, 178.4 mmol) and 3-bromo-2-methyl-propene (9.0 mL, 89.2 mmol). Purification by column chromatography eluting with 15% EtOAc in hexanes gave a pale yellow solid (7.80 g, 39% yield). 1H NMR (400 MHz, CDCl3) δ 7.13-7.22 (m, 2 H) 6.66 (t, J=2.27 Hz, 1 H) 5.81 (s, 1 H) 5.06-5.16 (m, 1H) 4.93-5.04 (m, 1H) 4.44 (s, 2 H) 3.91 (s, 3 H) 1.68-1.94 (m, 3 H); LCMS for C12H14O4 m/z 223.10 (M+H)+.