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

HRID 268703ノート

反応式

HRID 268703 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 18348522Ethyl 4-(3-chloropropoxy)benzoate

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4b1266b4c0a54aa183d5e20eefbdd13a
出典データセット
uspto-grants-2008_11
特許番号
US07446103B2

反応ノート

読み込み中…