Formaldehyde → Methyl tropate

A nitrogen purged 500 mL three-neck flask was charged with sodium bicarbonate (1.05 g; 0.013 mole), paraformaldehyde (17.37 g; 0.55 mole) and dimethyl sulfoxide (100 mL). Methyl phenylacetate (75.09 g; 0.5 mole) was added and rinsed in with dimethylsulfoxide (50 mL). The slurry was stirred magnetically and the temperature rose from 22° C. to 34° C. over 40 minutes. The temperature remained at 33°-35° C. for about one hour, after which the temperature was raised to 45°-46° C. and held for 12 hours. The reaction mixture was allowed to cool with stirring for about seven hours. A solution of tartaric acid (1.88 g) in dimethylsulfoxide (6 mL) was added, and the solvent was distilled at pot temperature 45° C. to 88° C. at 0.25 mm Hg. The distillate g) was retained. The pale yellow oily residue (97.79 g) which contained a small amount of white solid(sodium hydrogen tartrate) was filtered, then fractionally distilled to give a main cut (59.1 g) of methyl tropate b.p. 106°-112° C. (0.2 mm. Hg).

1. customA nitrogen purged 500 mL three-neck flask
2. washrinsed in with dimethylsulfoxide (50 mL)
3. waitThe temperature remained at 33°-35° C. for about one hour
4. temperatureafter which the temperature was raised to 45°-46° C.
5. waitheld for 12 hours
6. temperatureto cool
7. stirringwith stirring for about seven hours
8. additionA solution of tartaric acid (1.88 g) in dimethylsulfoxide (6 mL) was added
9. distillationthe solvent was distilled at pot temperature 45° C. to 88° C. at 0.25 mm Hg
10. filtrationwas filtered
11. distillationfractionally distilled

ORD record

ord-11bfa427346949b58b2a41e4ba74ce90

Source dataset

uspto-grants-1993_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05250744