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

HRID 1662367Notes

Reaction equation

[CH3:1][C:2]1([CH3:24])[C:6]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=2[O:17]C2CCCCO2)[C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH2:4][CH2:3]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CO>[CH3:1][C:2]1([CH3:24])[C:6]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=2[OH:17])[C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH2:4][CH2:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

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).

Workup

customthe organic solvent was removed under reduced pressure
customthe product was then purified on silica gel (0-15% EtOAc in hexanes)

Sources & evidence

ORD record: ord-de3d058c8b114b50a412db09655b12f6
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Reaction notes

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