Propargyl alcohol → 3-(4-Chlorophenyl)prop-2-yn-1-ol

HRID 1018659Notes

Reaction equation

HRID 1018659 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH2:9]([OH:12])[C:10]#[CH:11].C(N(CC)CC)C.CCCCCC>C(Cl)(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:11]#[C:10][CH2:9][OH:12])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 7859Propargyl alcoholHCID 8058HexaneHCID 8471TriethylamineHCID 125101-Chloro-4-iodobenzene

Product 1

HCID 41117183-(4-Chlorophenyl)prop-2-yn-1-ol

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 6 g of 1-chloro-4-iodo-benzene, 1.8 ml of propargyl alcohol and 5.2 ml of triethylamine in 30 ml of chloroform is placed under a nitrogen atmosphere. 208 mg of bis(triphenylphosphine)palladium(II) dichloride and 98 mg of copper(I) iodide are added thereto. The reaction mixture is stirred for one hour at 40° C. 300 ml of hot n-hexane are then added. The n-hexane phase is decanted off. The residue is again digested with 200 ml of hot n-hexane, and the n-hexane phase is decanted off. The n-hexane phases are concentrated and the residue is subjected to flash chromatography on silica gel with ethyl acetate/n-hexane (1:4), yielding 3-(4-chloro-phenyl)-2-propyn-1-ol, which can be recrystallised from n-hexane, m.p. 78-80° C.

Workup

  1. customThe n-hexane phase is decanted off
  2. customthe n-hexane phase is decanted off
  3. concentrationThe n-hexane phases are concentrated

Sources & evidence

ORD record
ord-e77121f440d541d483681898b006e8ff
Source dataset
uspto-grants-2002_11
Patent number
US06482859B1

Reaction notes

Loading…