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

HRID 253241노트

반응식

HRID 253241 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cc1deea9b25949c18538cc00c06bfae1
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872014B2

반응 노트

불러오는 중…