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

HRID 1377832ノート

反応式

HRID 1377832 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>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][O:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([Cl:8])[CH:10]=1)[CH3:7]

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, 1H), 6.95-6.82 (m, 2H), 6.75-6.70 (m, 1H), 4.53 (s, 2H), 4.21 (q, J=7.2 Hz, 2H), 1.23 (t, J=7.2 Hz, 3H).

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-ad2f4c03402d49fc982ffaecdb3548c7
出典データセット
uspto-grants-1997_09
特許番号
US05665773

反応ノート

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