Water → Hexanoic acid, 5-oxo-, 1,1-dimethylethyl ester

HRID 1486441노트

반응식

HRID 1486441 반응식
[O:1]=[C:2]([CH3:9])[CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].C(=O)(O)[O-].[Na+].O.C(O[C:20]([CH3:23])([CH3:22])[CH3:21])(=O)C>C(OCC)(=O)C.Cl(O)(=O)(=O)=O>[O:1]=[C:2]([CH3:9])[CH2:3][CH2:4][CH2:5][C:6]([O:8][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:7]

참가 물질

7

반응물 4

HCID 962WaterHCID 10908tert-Butyl acetateHCID 184074-Acetylbutyric acidHCID 516892Sodium Bicarbonate

생성물 1

HCID 11008632Hexanoic acid, 5-oxo-, 1,1-dimethylethyl ester수율 85%

시약·촉매·용매 2

HCID 24247Perchloric Acid촉매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 5-oxohexanoic acid (25 g, 192 mmol) in t-butyl acetate (600 mL) was added perchloric acid (500 μL, 8.31 mmol) and the resulting pale yellow solution was allowed to stir at room temp, with a drying tube in place, for 65 h. The reaction was diluted with ethyl acetate (400 mL) and then quenched with a mixture of sodium bicarbonate (50 g, 595 mmol) and water (100 mL). The organic layer was extracted with saturated aqueous sodium bicarbonate (5×150 mL), water (1×100 mL), brine (1×75 mL), dried over sodium sulfate, and filtered. The solvent was removed in vacuo to give the title compound (30.55 g, 85%) as a light oil. 1H NMR (500 MHz, chloroform-d) δ 2.50 (t, J=7.2 Hz, 2H), 2.25 (t, J=7.3 Hz, 2H), 2.16 (s, 3H), 1.89-1.83 (m, 2H), 1.46 (s, 9H).

후처리

  1. extractionThe organic layer was extracted with saturated aqueous sodium bicarbonate (5×150 mL), water (1×100 mL), brine (1×75 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-97419ed876804c7b85937fbe14b541af
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09427442B2

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