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

HRID 907506

反応式

HRID 907506 の反応式
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+].[CH2:24]([OH:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].O>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:30][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:4])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

参加物

6

反応物 3

HCID 962WaterHCID 81031-HexanolHCID 46945113Sodium 2,2-bis(hexyloxy)propyl sulfate

生成物 1

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

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d039f03c66d347b69941deabac3d4dd9
出典データセット
uspto-grants-2011_09
特許番号
US08013179B2

関連ノート

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