Hydrochloric Acid → HCID 21388144, compound

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Reaction Steps

A mixture of 4 -methyl-4(4-methyl-1,4-cyclohexadien-1-yl)pentanoic acid (45.3 g, 0.22 mol), potassium t-butoxide (102 g, 0.91 mmol), toluene (110 ml) and dimethyl sulfoxide (1,000 ml) was stirred for 24 hours at room temperature. The solution was cooled, brought to neutral pH with hydrochloric acid, poured into 2 liters saturated sodium chloride, and extracted with methylene chloride. After the solution was washed with saturated sodium chloride solution and the solvent removed, the residual oil was distilled to yield 41.3 g (65.2%) of the 4-methyl-4(4-methyl-1,3-cyclohexadien-1-yl) pentanoic acid: bp 136°-138° (1 mm); nD20 1.5029; δmax 264 nm; δTMSCDCl3 11.15 (s,1), 5.62 (s,2), 2.06 (s,4) 1.78 (s,3), 1.05 (s,6).

Provenance & Evidence