Hydrochloric Acid → 3-(3,4-Dichlorophenyl)-2-propene-1-ol acetate

HRID 357238

반응식

HRID 357238 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[Cl:8].N1C=CC=CC=1.[CH3:19][C:20](Cl)=[O:21].Cl>C(Cl)Cl.CN(C1C=CC=CN=1)C>[C:20]([O:12][CH2:11][CH:10]=[CH:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)(=[O:21])[CH3:19]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 537091912-Propen-1-ol, 3-(3,4-dichlorophenyl)-

생성물 1

HCID 538528443-(3,4-Dichlorophenyl)-2-propene-1-ol acetate수율 97%

시약·촉매·용매 2

HCID 218852-Dimethylaminopyridine촉매HCID 6344Dichloromethane용매

반응 조건

온도
23 °C

실험 절차

Treat a solution of the product of step 2 (13.2 g, 65 mmol) in CH2Cl2 (250 mL) at 0° C. with pyridine (7.89 mL, 97.5 mmol, 1.5 eq) and dimethylaminopyridine (397 mg, 3.25 0.05 eq), followed by CH3COCl (6.48 mL, 74.75 mmol, 1.15 eq). Allow the mixture to warm to 23° C., pour into 1M HCl (100 mL) and wash the resulting organic layer again with 1 M HCl (100 mL), followed by water (5×100 mL; pH=6.5-7). Dry the organic layer (Na2SO4) and concentrate to obtain 15.4 g (62.9 mmol, 97%) of 3-(3,4-dichlorophenyl)-2-propene-1-ol acetate as a colorless oil.

후처리

  1. washwash the resulting organic layer again with 1 M HCl (100 mL)
  2. dry with materialDry the organic layer (Na2SO4)
  3. concentrationconcentrate

출처 및 근거

ORD 기록
ord-596ba5ac38d843dda8fd994e96809546
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840725

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