[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].Br[CH2:14][CH2:15][OH:16].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.C(OCC)(=O)C>[OH:16][CH2:15][CH2:14][O:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12]
To a solution of methyl 4-hydroxy-3-methyl-benzoate (5.77 g, 34.7 mmol) in DMF (17 mL) was added 2-bromoethanol (6.51 g, 3.7 mL, 52.1 mmol) and cesium carbonate (33.95 g, 104.2 mmol) and the reaction mixture was heated at 60° C. for 16 hours. The reaction mixture was cooled to room temperature and then partioned between water (250 mL) and ethyl acetate (2×100 ml). The organic layers were combined, dried over Na2SO4, filtered and concentrated in vacuo to yield a crude oil that was purified by silica gel column chromatography using EtOAc/hexanes (10 to 100%) as eluent to give methyl 4-(2-hydroxyethoxy)-3-methyl-benzoate (1.87 g, 26%) as a white solid. ESI-MS m/z calc. 210.1. Found 211.1 (M+1)+; Retention time: 1.08 minutes (3 min run); 1H NMR (400 MHz, CDCl3) δ 7.94-7.79 (m, 2H), 6.84 (d, J=8.5 Hz, 1H), 4.23-4.08 (m, 2H), 4.08-3.96 (m, 2H), 3.88 (s, 3H), 2.34-2.18 (m, 3H).
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