Methyl 4-Formylbenzoate → HCID 20071004, compound

Participants

Reaction Steps

In analogy to Example 1B (1st paragraph), from 6,7,8,9-tetrahydro-α,3,7,7-tetramethyl-5H-benzocycloheptene-2-methanol, there is obtained the corresponding phosphonium salt. 5.30 g of the phosphonium salt are suspended in 35 ml of tetrahydrofuran and deprotonized at 0° with 9.0 ml of 1.4M nBuLi (hexane) After 30 minutes, 2 30 g of methyl 4-formylbenzoate are added thereto and the mixture is stirred at room temperature for an additional 2 hours. The mixture is poured on to ice-water, extracted with Et2O, washed with water, dried and evaporated. Chromatography on silica gel (low-boiling petroleum ether/AcOEt=93/3), followed by crystallization from n-hexane, yields 560 mg of methyl p-[(E)-(6,7,8,9-tetrahydro-3,7,7-trimethyl-5H-benzocyclohepten-2-yl) propenyl]benzoate of m.p. 59°-60°.

Provenance & Evidence