Hydrochloric Acid → Ethyl 2-(3-chlorophenoxy)acetate

HRID 634865ノート

反応式

HRID 634865 の反応式
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].Cl>C(OCC)(=O)C.CC(C)=O>[Cl:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[O:15][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 79333-ChlorophenolHCID 11430Potassium Carbonate

生成物 1

HCID 735422Ethyl 2-(3-chlorophenoxy)acetate収率 87.2%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Acetone (320 ml), 75 g (450 mmol) of ethyl bromoacetate, and 40.0 g (310 mmol) of 3-chlorophenol were mixed together, then 69.8 g (505 mmol) of potassium carbonate was added. The mixture was mechanically stirred and heated to reflux for 4 h, and after cooling to room temperature, was poured into 350 mL of ethyl acetate. To this was then cautiously added 400 mL of 1M HCl, taking care to avoid excess foaming. The layers were separated and the aqueous layer was extracted with portions of ethyl acetate (3×200 mL). The combined organic layers were dried over MgSO4, filtered, concentrated, and the resulting solid was recrystallized from hexane to afford 58 g (87%) of 10 as a white solid, m.p.=39-40° C. 1H NMR δ 7.20-7.08 (m, 1 H), 6.95-6.82 (m, 2 H), 6.75-6.70 (m, 1 H), 4.53 (s, 2 H), 4.21 (q, J=7.2 Hz, 2 H), 1.23 (t, J=7.2 Hz, 3 H).

後処理

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with portions of ethyl acetate (3×200 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe resulting solid was recrystallized from hexane

出典と根拠

ORDレコード
ord-fc616e5b91c84719bc08d45f47d86e60
出典データセット
uspto-grants-2001_02
特許番号
US06184250B2

反応ノート

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