4-(2,5-DIMETHYLPHENYL)BUTYRIC ACID synthesis
- Product Name:4-(2,5-DIMETHYLPHENYL)BUTYRIC ACID
- CAS Number:1453-50-5
- Molecular formula:C7H11NO
- Molecular Weight:125.17
Yield:-
Reaction Conditions:
with sodium hydroxide in n-heptane;water at -10 - 0; for 2 h;
Steps:
4
To a mixture of 5 N NaOH (6.6 L, 33.0 mole) and heptane (3.75 L) was added cyclopropylamine (1.73 kg, 99%, 30.0 mole) at -10 to 0 0C. A solution of cyclopropyl carbonyl chloride (3.20 kg, 98%, 30.0 mole) in heptane (3.75 L) was then slowly charged while maintaining the batch at - 10 to 0 0C. The mixture was stirred at -5 0C for 2 h then filtered. The product cake was washed with cold (0-5 0C) brine (4.0 L x 2), then ice-cold water (4.0 L) and heptane (8.0 L). Oven drying at 40 0C under vacuum gave the amide as a white solid.A 7/1 mixture of two rotamers: NMR data for the major isomer:1H NMR (400 MHz, CDCl3) δ 6.20 (brd, H), 2.72-2.66 (m, IH), 1.35-1.28 (m, IH), 0.99-0.91 (m, 2H), 0.83-0.65 (m, 4H), 0.51-0.47 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 175.19, 22.89, 14.57, 7.23, 6.65.
References:
WO2007/38452,2007,A1 Location in patent:Page/Page column 11
1453-52-7
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1453-50-5
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