Hydrochloric Acid → 1-(4-Chlorophenyl)-2-cyclopropylethanol

HRID 1074320노트

반응식

HRID 1074320 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])[CH2:9][CH:10]=[CH2:11])=[CH:4][CH:3]=1.Br[CH2:14]Br.Cl>CCOCC.[Zn].[Cu]Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:12])[CH2:9][CH:10]2[CH2:14][CH2:11]2)=[CH:6][CH:7]=1

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 3024DibromomethaneHCID 27577711-(4-Chlorophenyl)-3-buten-1-ol

생성물 1

HCID 190783841-(4-Chlorophenyl)-2-cyclopropylethanol수율 44%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 62652Cuprous chloride촉매HCID 3283Diethyl Ether용매

실험 절차

Crude 4-(4-chlorophenyl)but-1-en-4-ol from the previous reaction (85.37 g, approximately 92% pure, approximately 430 mmol), zinc dust (121.5 g, 1.86 mol), copper(I) chloride (18.69 g, 187 mmol) and dibromomethane (163.6 g, 936 mmol) in dry ether (250 ml) were heated under reflux for 3 hours in a sonic bath and then poured into 2M hydrochloric acid. The mixture was extracted with ether and the extract washed with 2M hydrochloric acid and brine, dried and evaporated in vacuo. Chromatography [SiO2, hexane-ethyl acetate (90:10)] gave 1-(4-chlorophenyl)-2-cyclopropylethanol (37.24 g, 44% from 4-chlorobenzaldehyde).

후처리

  1. temperaturewere heated
  2. temperatureunder reflux for 3 hours in a sonic bath
  3. extractionThe mixture was extracted with ether
  4. washthe extract washed with 2M hydrochloric acid and brine
  5. customdried
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-5bcafa100fe04ffda690b6f9b6c612b9
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04973767

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