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

HRID 964736ノート

反応式

HRID 964736 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-40ee2ae586a84184b7ea6ec93be2af90
出典データセット
uspto-grants-1998_06
特許番号
US05770741

反応ノート

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