Guaiacol → Ethyl 2-(2-methoxyphenoxy)propanoate

HRID 348379Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15].Br[CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>CN(C=O)C.C(OCC)C>[CH2:21]([O:20][C:18](=[O:19])[CH:17]([O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH3:7])[CH3:23])[CH3:22]

Participants

Conditions

Temperature: 90 °C

Procedure

Cesium carbonate (53.86 g, 165.3 mmol) was added to a solution of 2-methoxyphenol (10.26 g, 82.6 mmol) in anhydrous DMF (500 mL) at room temperature under an atmosphere of nitrogen. After five minutes, ethyl 2-bromopropionate (10.7 mL, 82.6 mmol, d=1.394) was added rapidly dropwise and the resultant mixture was allowed to stir at 90° C. for 18 h. The reaction mixture was diluted with diethyl ether, then extracted twice with 1N HCl and twice with water. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (25% ether in hexanes) to provide the titled compound (16.97 g, 92%) as a light yellow oil.1H NMR (400 MHz, CDCl3): δ 6.96–6.80 (m, 4H), 4.73 (q, 1H, J=7.04 Hz), 4.23–4.12 (m, 2H), 3.82 (s, 3H), 1.62 (d, 3H, J=6.65 Hz), 1.21(t, 3H, J=7.04 Hz). MS [ES+] m/z exact mass calcd for C12H17O4 225.1127, found 225.1110. Rf=0.19 in 25% ether in hexanes.

Workup

extractionextracted twice with 1N HCl and twice with water
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (25% ether in hexanes)

Sources & evidence

ORD record: ord-06bfea1d154c44488061a9a978aca66e
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176224B2

Reaction notes

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