Methane → Octyl 2-hydroxy-4-(methylthio)butanoate

HRID 1754036

反応式

HRID 1754036 の反応式
[OH:1][CH:2]([CH2:6][CH2:7][S:8][CH3:9])[C:3]([OH:5])=[O:4].C.[CH2:11](O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].S([O-])(O)(=O)=O.[Na+]>O.C1(C)C=CC=CC=1>[OH:1][CH:2]([CH2:6][CH2:7][S:8][CH3:9])[C:3]([O:5][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:4]

参加物

7

反応物 4

HCID 297MethaneHCID 9571-OctanolHCID 11427alpha-Hydroxy-gamma-methylmercaptobutyric acid2 回HCID 516919Sodium Bisulfate

生成物 1

HCID 86689968Octyl 2-hydroxy-4-(methylthio)butanoate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

To a multi-neck 5 L round bottom flask fitted with a mechanical stirrer, reflux condenser, and dean stark trap was added 2-hydroxy-4-(methylthio)butanoic acid (650 g, 4.33 mol, obtained for example by stirring Alimet over activated charcoal, filtering and concentrating in a rotovap), 1-octanol (845.4 g, 6.49 mol), sodium hydrogen sulfate (10.4 g, 86 mmol), and toluene (2.7 L).The resulting solution was heated to reflux with removal of water (˜146 mL) during the course of about 5.5 hours and the reaction was monitored by GC analysis. The reaction was cooled to room temperature overnight and then washed with saturated NaHCO3 (1×1.5 L), DI water (1×1.5 L) and brine (1×1.5 L), dried over sodium sulfate, filtered and evaporated to give a dark oil (1,525 g). The oil was purified by kugelrohr distillation at 130-150° C. and 0.1 mm Hg vacuum to give a pale yellow oil (507.6 g, 45%). m/z 285 (MNa+).

後処理

  1. customTo a multi-neck 5 L round bottom flask fitted with a mechanical stirrer
  2. temperaturereflux condenser, and dean stark trap
  3. filtrationfiltering
  4. temperaturewas heated
  5. washwashed with saturated NaHCO3 (1×1.5 L), DI water (1×1.5 L) and brine (1×1.5 L)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-e62949eb12f340c0acc79a4bb205d34e
出典データセット
uspto-grants-2015_10
特許番号
US09169203B2

関連ノート

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