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Sodium (11 g, spheres) was added to 200 ml ethanol with stirring. When the gas evolution ceased, methyl 3-chlorobenzoate (10 g, 0.057 mole) and dimethyl succinate (9.0 g, 0.615 mole) were added rapidly and the mixture was stirred for 5 minutes at room temperature. The mixture was slowly concentrated on a rotary evaporator to yield a greenish paste which was slurried in 100 ml ether and an additional 2 ml of dimethyl succinate was added. The reaction was evaporated to a paste, quenched with water and extracted with ether. The ether extracts were washed with water and brine, dried and evaporated in vacuo.

1. stirringthe mixture was stirred for 5 minutes at room temperature
2. concentrationThe mixture was slowly concentrated on a rotary evaporator
3. customto yield a greenish paste which
4. customThe reaction was evaporated to a paste
5. customquenched with water
6. extractionextracted with ether
7. washThe ether extracts were washed with water and brine
8. customdried
9. customevaporated in vacuo