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

HRID 964736Notes

Reaction equation

HRID 964736 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 62652Cuprous chlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-40ee2ae586a84184b7ea6ec93be2af90
Source dataset
uspto-grants-1998_06
Patent number
US05770741

Reaction notes

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