Hydrochloric Acid → 1,3-Dimethyl 2-(4-chlorophenyl)propanedioate

At 35° C. a solution of 4-chlorophenylacetic acid methyl ester (52 g) in THF (170 ml) was carefully added over a period of 70 min to a suspension of NaH (15.6 g) in dry THF (550 ml). Stirring was continued for 40 min without heating and the temperature dropped to 290C. The evolution of gas had stopped before dimethylcarbonate (94.8 ml) was added dropwise while the temperature of the mixture was maintained at 25–28° C. After the evolution of gas had ceased, the mixture was diluted with THF (200 ml) and stirring was continued for 72 h at rt. The mixture was carefully acidified with aq. HCl before bulk of the THF was removed in vacuo. The residue was dissolved in diethyl ether (1200 ml), washed three times with 1 N aq. HCl and once with brine, dried over MgSO4 and evaporated. The residue formed was collected, washed with diethyl ether and dried to give 2-(4-chloro-phenyl)-malonic acid dimethyl ester (42 g) as white crystals.

1. temperaturewithout heating
2. additionwas added dropwise while the temperature of the mixture
3. temperaturewas maintained at 25–28° C
4. stirringstirring
5. waitwas continued for 72 h at rt
6. customwas removed in vacuo
7. dissolutionThe residue was dissolved in diethyl ether (1200 ml)
8. washwashed three times with 1 N aq. HCl
9. dry with materialonce with brine, dried over MgSO4
10. customevaporated
11. customThe residue formed
12. customwas collected
13. washwashed with diethyl ether
14. customdried

ORDレコード

ord-e37da2d3f11443b5b8ecacc187d5f905

出典データセット

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07091201B2