Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Methyl 3-(5,5-dimethylcyclopent-1-enyl)-4-hydroxybenzoate

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Reaction Conditions

Reaction Steps

To a stirred solution of 66.6G (19.0 g, 57.6 mmol) in MeOH (150 mL) was added PPTS (1.46 g, 5.80 mmol). The mixture was heated to 50° C. and monitored with TLC. After 19 hours, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-15% EtOAc in hexanes) to yield 66.6H as a white solid (yield 90%). 1H NMR (400 MHz) (CDCl3) δ ppm 7.89 (1H, dd, J=8.6, 2.0 Hz), 7.79 (1H, d, J=2.3 Hz), 6.97 (1H, d, J=8.6 Hz), 5.87 (1H, s), 5.81 (1H, t, J=2.3 Hz), 3.89 (3H, s), 2.51 (2H, td, J=7.1, 2.5 Hz), 1.94 (2H, t, J=7.0 Hz), 1.12 (6H, s).

Provenance & Evidence