Water → Hexyl 2,2-bis(hexyloxy)propanoate

HRID 907508

반응식

HRID 907508 반응식
S([O-])([O:4][CH2:5][C:6]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:7])(=O)=O.[Na+].[OH2:24]>C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>[CH2:9]([O:8][C:6]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])([CH3:7])[C:5]([O:24][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:4])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

참가 물질

5

반응물 2

HCID 962WaterHCID 46945113HCID 46945113, 화합물2회

생성물 1

HCID 46945489Hexyl 2,2-bis(hexyloxy)propanoate수율 84%

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 1140Toluene용매

실험 절차

To a solution of methyl pyruvate 1 (10.0 g, 98.0 mmol) in toluene (100 mL) is added 1-hexanol 2 (40.1 g, 392 mmol) and p-TsOH (186 mg, 0.98 mmol). The mixture is heated to reflux for 10 hours with azeotropic removal of water from the reaction mixture. The reaction is quenched with saturated NaHCO3 (100 mL), and the reaction mixture is extracted with ethyl acetate (2×100 mL). The combined organic layers are washed with brine (100 mL) and dried over anhydrous sodium sulfate. The solvent is removed and the residue is purified by silica gel chromatography (1→10% ethyl acetate/hexane) to give hexyl 2,2-bis(hexyloxy)propanoate 3 (29.5 g, 84%) as a colorless oil: Rf (15% EtOAc/hexane)=0.53; IR (thin film, cm−1) 2956, 2930, 2860, 1746 (C═O), 1467, 1280, 1137, 1062. 1H NMR (600 MHz, CDCl3) δ 4.14 (t, J=7.2 Hz, 2H), 3.48 (ddd, J=9.0, 7.2, 6.6 Hz, 2H), 3.35 (ddd, J=9.0, 7.2, 6.6 Hz, 2H), 1.65-1.63 (m, 2H), 1.59-1.54 (m, 4H), 1.49 (s, 3H), 1.35-1.24 (m, 18H), 0.86 (t, J=7.2 Hz, 9H); 13C NMR (150 MHz, CDCl3) δ 170.2, 99.5, 65.4, 62.6, 31.7, 31.3, 29.7, 28.5, 25.8, 25.5, 22.6, 22.5, 21.9, 14.0, 13.9.

후처리

  1. temperatureThe mixture is heated
  2. customThe reaction is quenched with saturated NaHCO3 (100 mL)
  3. extractionthe reaction mixture is extracted with ethyl acetate (2×100 mL)
  4. washThe combined organic layers are washed with brine (100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent is removed
  7. customthe residue is purified by silica gel chromatography (1→10% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-270782f1fbaf49b09bb55f3242803f29
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08013179B2

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