Ethanol → HCID 57718928, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(p-methoxyphenyl)-cyclopentanecarboxylic acid 093909 (5.0 g, 22.7 mmol) in ethanol (50 mL) was treated with conc. H2SO4 (4.40 g, 44.9 mmol) and heated to reflux under N2 for 12 h. The reaction was cooled and the solvent removed in vacuo to give a residue that was extracted with EtOAc and water. The organic layer was dried (MgSO4) and the solvent removed in vacuo to 5.93 g crude ester (100%) that was utilized without purification. The ester (5.93 g, assume 22.7 mmol) was dissolved in dry CH2Cl2 (75 mL), cooled to −78° C. and then treated dropwise with BBr3 (11.4 g, 45.6 mmol). The reaction was warmed to 0° C. for 15 minutes and then quenched with methanol then water. The reaction mixture was extracted with CH2Cl2 and water, the organic layer was dried (MgSO4), and the solvent removed in vacuo to give crude product that was purified by flash chromatography using 6:1 hexanes:EtOAc to afford 4.34 g (79%) 1-(4-hydroxy-phenyl)-cyclopentanecarboxylic acid ethyl ester. MS (ES+) Calc'd for C14H19O3 (M+1) 235. Found m/z 235 (100%). 1H NMR.

Provenance & Evidence