Sulfuric Acid → 2-(4-Chlorophenyl)-5-hydroxyoct-1-ene

HRID 462880Notes

Reaction equation

HRID 462880 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:13])[CH2:9][CH2:10][CH:11]=[O:12])=[CH:4][CH:3]=1.[CH2:14]([Mg]I)[CH2:15][CH3:16].S(=O)(=O)(O)O>C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH2:9][CH2:10][CH:11]([OH:12])[CH2:14][CH2:15][CH3:16])=[CH2:13])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 11008833HCID 11008833, compoundHCID 178455858HCID 178455858, compound

Product 1

HCID 132358192-(4-Chlorophenyl)-5-hydroxyoct-1-eneYield 77.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 4-(4-chlorophenyl)pent-4-enal (2.0 g) in dry diethyl ether (25 ml) was added to a stirred solution of propylmagnesium iodide [from 1-iodopropane (2.72 g) and magnesium turnings (0.48 g)] in dry diethyl ether (50 ml) under an atmosphere of nitrogen (exotherm). After stirring for 1 hour the reaction mixture was poured into a mixture of ice and dilute sulphuric acid, then extracted with ether. The extracts were washed with water, dried over magnesium sulphate, and concentrated under reduced pressure to give 2-(4-chlorophenyl)-5-hydroxyoct-1-ene (1.9 g, 77%) as a yellow oil.

Workup

  1. extractionextracted with ether
  2. washThe extracts were washed with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0ef0bd0c3c7e44658d6626d61555ba83
Source dataset
uspto-grants-1985_05
Patent number
US04518415

Reaction notes

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