Isobutyric Acid → 2,2-Dimethyl-3-phenylpropanoic acid

HRID 54230

반응식

HRID 54230 반응식
[H-].[Na+].C(NC(C)C)(C)C.[C:10]([OH:15])(=[O:14])[CH:11]([CH3:13])[CH3:12].C([Li])CCC.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CCCCCC.O.O1CCCC1>[CH3:12][C:11]([CH3:13])([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:10]([OH:15])=[O:14]

참가 물질

9

반응물 5

HCID 6590Isobutyric AcidHCID 7498Benzyl BromideHCID 7912DiisopropylamineHCID 24758Sodium hydrideHCID 178418339Butyllithium

생성물 1

HCID 218802,2-Dimethyl-3-phenylpropanoic acid수율 15%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
0 °C

실험 절차

To a mixture of 1.23 g (41.0 mmol) of 80% sodium hydride and 50 mL of anhydrous tetrahydrofuran under a nitrogen atmosphere, was added 3.88 g (38.3 mmol) of diisopropylamine and then 3.3 g (37.5 mmol) of isobutyric acid. After heating at reflux for 5 minutes and cooling to 0° C., 15 mL (37.5 mmol) of 2.5M n-butyllithium in hexane was added. The mixture was warmed to 35° C. for 30 min, cooled to 0° C. and 6.40 g (37.5 mmol) of benzyl bromide added. The mixture was stirred for 30 minutes at 0° C., then warmed to 35° C. for one hour and recooled to 0° C. Water was added and the aqueous layer extracted with diethyl ether, acidified with 6N aqueous HCl and extracted with diethyl ether. The organic layer was dried and concentrated to provide 4.0 g of crude product. Chromatography on silica gel using 10% methanol/methylene chloride afforded 1.0 g of pure 2,2-dimethyl-3-phenylpropionic acid, m/e 185 (M+Li).

후처리

  1. temperatureAfter heating
  2. temperatureat reflux for 5 minutes
  3. temperatureThe mixture was warmed to 35° C. for 30 min
  4. temperaturecooled to 0° C.
  5. temperaturewarmed to 35° C. for one hour
  6. customrecooled to 0° C
  7. extractionthe aqueous layer extracted with diethyl ether
  8. extractionextracted with diethyl ether
  9. customThe organic layer was dried
  10. concentrationconcentrated
  11. customto provide 4.0 g of crude product

출처 및 근거

ORD 기록
ord-f054f2770ff34f30b310220b4e49049a
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622949

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