Acetic Acid → 3-(3'-p-Chlorobenzyl-phenyl)-propionic acid
Reaction equation
C(OCC)(=O)CC(O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13](=O)[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH:8]=1)=O.S(=O)(=O)(O)O.O.[C:32]([OH:35])(=[O:34])[CH3:33]>>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][C:9]2[CH:8]=[C:7]([CH2:6][CH2:33][C:32]([OH:35])=[O:34])[CH:12]=[CH:11][CH:10]=2)=[CH:19][CH:18]=1Participants
Procedure
A solution of 15.2 g of ethyl 3-(p-chlorobenzoyl)-benzyl malonate in 50 ml of acetic acid was added to a solution of 50 ml of sulfuric acid and 50 ml of water and the mixture was refluxed under a nitrogen atmosphere for 20 hours and then cooled to room temperature. The mixture was poured into water and then extracted with methylene chloride. The organic phase was extracted with N sodium hydroxide and the alkaline phase was treated with activated carbon, filtered and acidified by addition at 10° C with stirring of 270 ml of N hydrochloric acid. The mixture was vacuulm filtered and the precipitate was washed with water and dried under reduced pressure to obtain 3.11 g of 3-(3'-p-chlorobenzyl-phenyl)-propionic acid which was used as is for the next step.
Workup
- temperaturethe mixture was refluxed under a nitrogen atmosphere for 20 hours
- extractionextracted with methylene chloride
- extractionThe organic phase was extracted with N sodium hydroxide
- additionthe alkaline phase was treated with activated carbon
- filtrationfiltered
- additionacidified by addition at 10° C
- filtrationThe mixture was vacuulm filtered
- washthe precipitate was washed with water
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-3756918f719a41fb87c224184bd78dc3
- Source dataset
- uspto-grants-1976_11
- Patent number
- US03995056
Reaction notes
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