Triethylamine → 1-(Chloromethyl)-2,3-bis{[2-(methyloxy)ethyl]oxy}benzene

HRID 253241ノート

反応式

HRID 253241 の反応式
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:17]O.C(N(CC)CC)C.S(Cl)([Cl:28])=O>ClCCl>[Cl:28][CH2:17][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH2:13][CH2:14][O:15][CH3:16])[C:6]=1[O:5][CH2:4][CH2:3][O:2][CH3:1]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 66889790(2,3-Bis{[2-(methyloxy)ethyl]oxy}phenyl)methanol

生成物 1

HCID 668913101-(Chloromethyl)-2,3-bis{[2-(methyloxy)ethyl]oxy}benzene収率 96%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of (2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)methanol (1.12 g, 4.37 mmol) and triethylamine (0.49 g, 4.84 mmol) in dichloromethane (20 mL) was slowly added thionyl chloride (0.78 g, 6.58 mmol) at 0° C. The solution was stirred at 0° C. for 15 min, and then at rt for 3 h. Dichloromethane (80 mL) was added, the solution was washed with water (50 mL), sat. sodium bicarbonate (50 mL), and brine (50 mL), dried with sodium sulfate, and concentrated to give crude 1-(chloromethyl)-2,3-bis{[2-(methyloxy)-ethyl]oxy}benzene (1.15 g, 96% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ7.02 (m, 2H), 6.90 (dd, 1H), 4.72 (s, 2H), 4.27 (m, 2H), 4.14 (m, 2H), 3.77 (m, 2H), 3.73 (m, 2H), 3.46 (s, 3H), 3.44 (s, 3H).

後処理

  1. customat 0° C
  2. waitat rt for 3 h
  3. washthe solution was washed with water (50 mL), sat. sodium bicarbonate (50 mL), and brine (50 mL)
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-cc1deea9b25949c18538cc00c06bfae1
出典データセット
uspto-grants-2011_01
特許番号
US07872014B2

反応ノート

読み込み中…