Ethanol → 843661-24-5

Participants

Reaction Conditions

Reaction Steps

To a round-bottomed flask was added methyl 4-[(4-hydroxyphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]benzoate (25) (8.06 g, 21 mmoL), EtOH (100 mL), and THF (100 mL). To the solution was added 1 N aqueous NaOH (200 mL). The reaction mixture was stirred at 65° C. under a nitrogen atmosphere for 3 h. The reaction mixture was partially concentrated in vacuo to remove the EtOH and THF. The aqueous mixture was cooled in an ice-water bath and 1 N aqueous HCl was slowly added to pH ˜1. The acidic aqueous suspension was extracted with CH2Cl2 (1×) followed by EtOAc (3×). Those EtOAc extracts that contained the majority of product, as indicated by TLC, were independently washed with brine, combined, dried over MgSO4, filtered, and the filtrate was concentrated to give 6.0 g of the crude product as a pale tan solid. The CH2Cl2 extract noted above was concentrated to give 1.9 g of the crude product as an off-white solid. The two crops of crude product were combined and purified by flash chromatography on silica gel with CH2Cl2:MeOH (95:5) to give 6.07 g (79%) of compound 26 as a white solid. A portion of the product was dried under vacuum at 90° C. to give the following 1H NMR data. 1H NMR (400 MHz, DMSO-d6): δ 0.86 (s, 6H), 0.88 (s, 6H), 1.24 (s, 2H), 1.85 (s, 2H), 1.92 (s, 2H), 6.66 (d, J=8.5 Hz, 2H), 6.93 (d, J=8.4 Hz, 2H), 7.22 (d, J=8.3 Hz, 2H), 7.84 (d, J=8.3 Hz, 2H), 9.30 (s, 2H), 12.78 (br s, 1H). The compound was silylated prior to EI analysis. HRMS (EI) Calcd for C30H44O3Si2: 508.2829 (M+.). Found: 508.2833.

Provenance & Evidence