反応 #76265

反応方程式

2,12-Bis-(4-isobutyl-phenyl)-2,12-dimethyl-7-oxo-tridecanedioic acid diethyl ester

water

potassium hydroxide

→

2,12-bis-(4-isobutyl-phenyl)-2,12-dimethyl-7-oxo-tridecanedioic acid

収率 86.2%

溶媒

ethanol

反応条件

後処理

1. 1
   温度The solution was heated
2. 2
   温度to reflux for six hours
3. 3
   温度cooled
4. 4
   濃縮concentrated
5. 5
   その他After the ethanol was removed
6. 6
   workup.ADDITIONwater (200 mL) was added
7. 7
   抽出the solution was extracted with diethyl ether (100 mL)
8. 8
   抽出The product was then extracted with diethyl ether (2×100 mL)
9. 9
   乾燥dried with sodium sulfate (5 g)
10. 10
    ろ過After filtration, concentration
11. 11
    その他drying under high vacuum

実験手順

2,12-Bis-(4-isobutyl-phenyl)-2,12-dimethyl-7-oxo-tridecanedioic acid diethyl ester (3.0 g, 4.95 mmol) was dissolved in ethanol (40 mL) and water (10 mL) with potassium hydroxide (4.4 g 85%). The solution was heated to reflux for six hours, cooled and concentrated. After the ethanol was removed, water (200 mL) was added and the solution was extracted with diethyl ether (100 mL). The aqueous fraction was acidified with concentrated hydrochloric acid (10 mL, to pH=1). The product was then extracted with diethyl ether (2×100 mL). The ether fractions were combined and dried with sodium sulfate (5 g). After filtration, concentration and drying under high vacuum, the reaction yielded 2,12-bis-(4-isobutyl-phenyl)-2,12-dimethyl-7-oxo-tridecanedioic acid (2.35 g, 82% yield) as a light yellow foam. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm) 10.02 (bs, 2H), 7.24 (d, 4H, J=8.0 Hz), 7.09 (d, 4H, J=8.0 Hz), 2.43 (d, 4H, J=7.0 Hz), 2.33 (t, 4H, J=7.3 Hz), 2.05-1.88 (m, 2H), 1.96-1.77 (m, 4H), 1.55-1.42 (m, 10H), 1.22-1.08 (m, 4H), 0.88 (d, 12H, J=6.6). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm): 211.48, 182.94, 140.43, 140.24, 129.27, 125.94, 49.71, 45.06, 42.58, 42.58, 38.91, 30.25, 24.45, 24.24, 22.58, 22.40. HRMS (LSIMS, nba): Calcd. for C35H50O5Na (MNa+): 573.3555, found: 573.3459.

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