Hexachloroethane → 4-Methoxy-3-methylbenzyl chloride

HRID 270155

Reaction equation

HRID 270155 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]O)=[CH:5][C:4]=1[CH3:11].[Cl:12]C(Cl)(Cl)C(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][Cl:12])=[CH:5][C:4]=1[CH3:11]

Participants

5

Reactant 3

HCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 14457544(4-Methoxy-3-methylphenyl)methanol

Product 1

HCID 1437424-Methoxy-3-methylbenzyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-methoxy-3-methylphenyl)methanol (2.31g, 15.18mmoles, 1eq) in anhydrous CH2Cl2(50ml, 0.3M) was added hexachloroethane (3.59g, 15.18mmoles, 1eq) and triphenylphosphine (3.98g, 15.18mmoles, 1eq). This mixture was stirred at room temperature overnight at which point the reaction was transferred to a separatory funnel and washed with H2O, brine, dried over Na2SO4, filtered, concentrated in vacuo and filtered through a plug of silica gel (30% EtOAc/Hexanes) to yield 2.59g (100%) of product.

Workup

  1. customwas transferred to a separatory funnel
  2. washwashed with H2O, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationfiltered through a plug of silica gel (30% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-b9176512d903468e9f304292a891a365
Source dataset
uspto-grants-2008_11
Patent number
US07449468B2

Linked notes

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