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

HRID 1074320ノート

反応式

HRID 1074320 の反応式
[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

参加物

7

反応物 3

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

生成物 1

HCID 190783841-(4-Chlorophenyl)-2-cyclopropylethanol収率 44%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 62652Cuprous chloride触媒HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5bcafa100fe04ffda690b6f9b6c612b9
出典データセット
uspto-grants-1990_11
特許番号
US04973767

反応ノート

読み込み中…