Allyl bromide → 3-Allyloxy-5-hydroxybenzoic acid methyl ester

Methyl 3,5-dihydroxybenzoate (20.9 g, 124 mmol) was dissolved in DMF (30 mL). Potassium carbonate (34.4 g, 249 mmol) was added, followed by allyl bromide (10.5 mL, 124 mmol). The resulting suspension was stirred at room temperature overnight under argon atmosphere. The reaction mixture was quenched with H2O, extracted with EtOAc (2×150 mL). The organic layers were washed with H2O (2×200 mL), dried with MgSO4 and concentrated in vacuo to yield a pale yellow oil which was purified by flash column chromatography eluting with 20% EtOAc in hexane to give a pale yellow solid (10.25 g, 40% yield). 1H NMR (400 MHz, CDCl3) δ 7.08-7.22 (m, 2 H) 6.65 (t, J=2.40 Hz, 1 H) 5.94-6.21 (m, 1 H) 5.73 (s, 1 H) 5.42 (dd, J=17.18, 1.52 Hz, 1 H) 5.31 (dd, J=10.48, 1.39 Hz, 1 H) 4.55 (d, J=5.05 Hz, 2 H) 3.91 (s, 3 H); LCMS for C14H12O4 m/z 209.0 (M+H)+.

1. customThe reaction mixture was quenched with H2O
2. extractionextracted with EtOAc (2×150 mL)
3. washThe organic layers were washed with H2O (2×200 mL)
4. dry with materialdried with MgSO4
5. concentrationconcentrated in vacuo
6. customto yield a pale yellow oil which
7. customwas purified by flash column chromatography
8. washeluting with 20% EtOAc in hexane

ORD record

ord-aa9d124b4ba14eff8279a22f10529702

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119624B2