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

HRID 1377832노트

반응식

HRID 1377832 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 735422Ethyl 2-(3-chlorophenoxy)acetate수율 87.2%

시약·촉매·용매 2

HCID 180Acetone용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ad2f4c03402d49fc982ffaecdb3548c7
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665773

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