4'-Hydroxyacetophenone → 1-[4-(3-Chloropropoxy)phenyl]ethanone

HRID 4726

反応式

HRID 4726 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14][Cl:15].[OH-].[K+]>CO>[Cl:15][CH2:14][CH2:13][CH2:12][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 74694'-HydroxyacetophenoneHCID 80061-Bromo-3-chloropropaneHCID 14797Potassium Hydroxide

生成物 1

HCID 126856131-[4-(3-Chloropropoxy)phenyl]ethanone収率 68%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a mixture of p-hydroxyacetophenone (50.7 g, 0.37 mol) and 1-bromo-3-chloropropane (160 ml, 1.5 mol) in methanol (250 ml) was added portionwise potassium hydroxide (63 g, 1.12 mol). The mixture was stirred at reflux for 24 hours, cooled to room temperature, filtered through Celite and evaporated in vacuo. The residual semi-solid was diluted with diethyl ether (500 ml) and washed with H2O (2×300 ml). The ether solution was dried over MgSO4, filtered and evaporated in vacuo to give p-chloropropoxy acetophenone as a liquid in 68% yield (53.38 g). 1H NMR (CDCl3): δ7.98-7.89 (d, J=8.9 Hz, 2H), 7.02-6.92 (d, J=8.9 Hz, 2H), 4.16 (t, J=5.9 Hz, 2H), 3.75 (t, J=6.4 Hz, 2H), 2.52 (s, 3H), 2.34-2.16 (m, 2H).

後処理

  1. temperatureat reflux for 24 hours
  2. filtrationfiltered through Celite
  3. customevaporated in vacuo
  4. additionThe residual semi-solid was diluted with diethyl ether (500 ml)
  5. washwashed with H2O (2×300 ml)
  6. dry with materialThe ether solution was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-79c238d7b16349c6ba9878c87b186e20
出典データセット
uspto-grants-1988_02
特許番号
US04727145

関連ノート

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