Benzyl Alcohol → Benzyl 4,5,6-trichloropicolinate

HRID 1913926

反応式

HRID 1913926 の反応式
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[CH:3]=1.C(O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10]([O:12][CH2:13][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:11])[CH:3]=1

参加物

4

反応物 2

HCID 244Benzyl AlcoholHCID 12993691Methyl 4,5,6-trichloropicolinate

生成物 1

HCID 86668437Benzyl 4,5,6-trichloropicolinate収率 97.9%

試薬・触媒・溶媒 1

HCID 11026Titanium isopropoxide触媒

反応条件

温度
100 °C

実験手順

A mixture of methyl 4,5,6-trichloropicolinate (25 g, 0.10 moles (mol)) and benzyl alcohol (100 g, 0.2 mol) in a 250 mL three-neck round bottom flask was heated under nitrogen at 100° C. Titanium isopropoxide (0.6 g, 0.02 mol) was added. After 4 h at 100° C., the nearly colorless solution was cooled and transferred to a 250 mL round bottom single neck flask. Excess benzyl alcohol was removed under vacuum to give a nearly white solid (31 g, 94%): mp 125-126.5° C.; 1H NMR (400 MHz, CDCl3) δ 8.08 (s, 1H, pyridine H), 7.42 (m, 2H, phenyl), 7.31 (m, 3H, phenyl), 5.40 (s, 2H, CH2Ph); 13C{1H} NMR (101 MHz, CDCl3) δ 162.0 (CO2R), 150.4, 145.0, 144.9, 134.7, 133.1, 128.3 (phenyl CH), 125.4 (pyridine CH), 67.88 (CH2Ph).

後処理

  1. temperaturethe nearly colorless solution was cooled
  2. customtransferred to a 250 mL round bottom single neck flask
  3. customExcess benzyl alcohol was removed under vacuum

出典と根拠

ORDレコード
ord-c4d8920af37b4d75832d466d5da9d7df
出典データセット
uspto-grants-2013_12
特許番号
US08609855B2

関連ノート

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