Hydrochloric Acid → 5-(2-Methylphenyl)-5-oxovaleric acid
Reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.[CH3:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[Mg]Cl.Cl>O1CCCC1>[O:6]=[C:5]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH3:9])[CH2:4][CH2:3][CH2:2][C:1]([OH:7])=[O:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A stirred solution of glutaric anhydride (22.82 g) in dry tetrahydrofuran (300 mL) at −78° C. is treated with a solution of 2-methylphenyl magnesium chloride in tetrahydrofuran (200 mL, 0.1 M) over 45 minutes. The mixture is stirred at −78° C. for 2.5 hours and the grey suspension is poured into 1 N hydrochloric acid (300 mL). The mixture is extracted with ethyl acetate (300 mL). The organic phase is dried over magnesium sulphate and evaporated to give 5-oxo-5-(2-methylphenyl)pentanoic acid (36.74 g) as a red-brown oil.
Workup
- extractionThe mixture is extracted with ethyl acetate (300 mL)
- dry with materialThe organic phase is dried over magnesium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-9a5a2d605f79416ea8c4086a1bbb5d8b
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06211234B1
Reaction notes
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