Oxalyl chloride → HCID 15572116, compound

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Reaction Steps

Oxalyl chloride (2.665 g., 1.79 mL, 0.021 mole) is added to a suspension of (5H dibenzo[a,d]cyclohepten-5-ylidene)acetic acid (5.000 g., 0.020 mole) in dry benzene (70 mL). An exothermic reaction occurs and the solid gradually dissolves. After solution is complete, the mixture is refluxed for one hour, then concentrated in vacuo to give an amber oil which crystallizes on storage at ambient temperature. Absolute methanol (75 mL) is added to the solid acid chloride. The mixture is stirred magnetically until complete solution is obtained, then refluxed for 45 minutes. The solvent is evaporated in vacuo to give a crystalline solid. The yield of crude ester melting at 83.5°-84.5° C. (uncorr.) is 5.210 g. (99.31%). Recrystallization of this material from methanol affords colorless rods melting at 86.0°-86.5° C. (uncorr.) in a yield of 3.508 g. (66.86%).

Provenance & Evidence