1-Bromo-3-chloropropane → Ethyl 4-(3-chloropropoxy)benzoate

HRID 268703노트

반응식

HRID 268703 반응식
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.Br[CH2:14][CH2:15][CH2:16][Cl:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:17][CH2:16][CH2:15][CH2:14][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1

참가 물질

5

반응물 3

HCID 80061-Bromo-3-chloropropaneHCID 8434EthylparabenHCID 11430Potassium Carbonate

생성물 1

HCID 18348522Ethyl 4-(3-chloropropoxy)benzoate

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Ethyl 4-hydroxybenzoate (60.0 g), 1-bromo-3-chloropropane (71.37 ml) and potassium carbonate (149.61 g) were heated under reflux in acetone (1445 ml) overnight. The reaction mixture was then allowed to cool to rt, filtered and evaporated. The residue was chromatographed [silica gel; step gradient 0-5% ethyl acetate/hexane]. Fractions containing pure product were combined and evaporated to give the subtitled compound as a clear oil (70.0 g). MS electrospray (+ion) 243 (MH+). 1H NMR δ (CDCl3): 8.00 (2H, d, J=8.8 Hz), 6.92 (2H, d, J=8.8 Hz), 4.36 (2H, q, J=7.1 Hz), 4.18 (2H, t, J=5.8 Hz), 3.74 (2H, t, J=6.2), 2.25 (2H, m), 1.37 (3H, t, J=7.1 Hz).

후처리

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue was chromatographed [silica gel; step gradient 0-5% ethyl acetate/hexane]
  4. additionFractions containing pure product
  5. customevaporated

출처 및 근거

ORD 기록
ord-4b1266b4c0a54aa183d5e20eefbdd13a
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446103B2

반응 노트

불러오는 중…