Ethanol → 2-(4-Methyl-phenoxy)-5-methyl-phenylacetic acid
Reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=2[CH2:14][C:15]#N)=[CH:4][CH:3]=1.C(O)C.[OH-:22].[K+].[OH2:24]>>[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=2[CH2:14][C:15]([OH:24])=[O:22])=[CH:4][CH:3]=1Participants
Procedure
A solution of 95 g. of crude 2-(4-methyl-phenoxy)-5-methyl-phenylacetonitrile in 500 ml. of ethanol is treated with a solution of 67 g. of potassium hydroxide in 120 ml. of water and heated to reflux for 5 hours. Then, the ethanol is evaporated in vacuo and the residue diluted with 500 ml. of water. The resulting mixture is extracted twice with ether. The ethereal extracts are extracted twice with sodium bicarbonate solution. The combined aqueous solutions are acidified and extracted three times with ether. The ethereal extracts are washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated in vacuo, and there is obtained 2-(4-methyl-phenoxy)-5-methyl-phenylacetic acid which, after recrystallization from methanol/water, melts at 101°-104° C.
Workup
- temperatureto reflux for 5 hours
- customThen, the ethanol is evaporated in vacuo
- additionthe residue diluted with 500 ml
- extractionThe resulting mixture is extracted twice with ether
- extractionThe ethereal extracts are extracted twice with sodium bicarbonate solution
- extractionextracted three times with ether
- washThe ethereal extracts are washed with saturated sodium chloride solution
- dry with materialdried over sodium sulfate
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-fcb03220970d41a584fea5122d8036e2
- Source dataset
- uspto-grants-1978_08
- Patent number
- US04105664
Reaction notes
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