4-(4-isobutylphenyl)-4-oxobutanoic acid synthesis
- Product Name:4-(4-isobutylphenyl)-4-oxobutanoic acid
- CAS Number:73120-67-9
- Molecular formula:C14H18O3
- Molecular Weight:234.29
Yield:73120-67-9 99%
Reaction Conditions:
Stage #1: succinic acid anhydride;1-phenyl-2-methylpropanewith aluminum (III) chloride in 1,1-dichloroethane at 20; for 1 h;Heating / reflux;
Stage #2: with hydrogenchloride in 1,1-dichloroethane;water at 20; for 0.166667 h;
Steps:
5 Example 5 [4-OXO-4-] (2'methylpropyl) phenylbutanoic acid
2'methylpropylbenzene [(5.] [0M,] 0.0373moles) and succinic anhydride (4. [5GM,] 0.0448 moles), were taken up in dichloroethane (50 ml). Aluminium chloride (10. [90G,] 0.0821 moles) was added at room temperature and the mixture heated under reflux for lhr with stirring. The reaction mixture was cooled to room temperature, diluted with 40 ml of a 1: 1 mixture of water and Cone. hydrochloric acid. After stirring for 10 min the reaction mixture was extracted with ethyl acetate (25ml). The ethyl acetate layer was dried and concentrated to give 8.7 gm (99%) of the title compound as a solid, mp [102-105°] C. [1H-NMR] (CDC13, [8)] : 7.83 (d, 2H), 7.17 (d, 2H), 3.24 (t, 2H), 2.74 (t, 2H), 2.46 (d, 2H), 1.80 (pent. , 1H).
References:
WO2004/26848,2004,A1 Location in patent:Page 34