Thionyl Chloride → 3-Methoxy-4-(2-propynyloxy)benzoyl chloride

HRID 1675571Notes

Reaction equation

HRID 1675571 reaction equation
[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[O:14][CH3:15])[C:2]#[CH:3].S(Cl)([Cl:18])=O>CN(C=O)C.C1(C)C=CC=CC=1>[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([Cl:18])=[O:10])=[CH:7][C:6]=1[O:14][CH3:15])[C:2]#[CH:3]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 131214803-Methoxy-4-(prop-2-ynyloxy)benzoic acid

Product 1

HCID 574456713-Methoxy-4-(2-propynyloxy)benzoyl chlorideYield 84.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

To 100 ml of toluene were added 12.0 g of 4-(2-propynyloxy)-3-methoxybenzoic acid, 9.0 g of thionyl chloride and 50 mg of DMF, and the resulting mixture was heated to reflux for 3 hours. Thereafter, the reaction mixture which had been allowed to cool to near room temperature was concentrated under reduced pressure. The resulting solid was washed with hexane, and 11.0 g of 4-(2-propynyloxy)-3-methoxybenzoyl chloride was obtained.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 3 hours
  3. concentrationwas concentrated under reduced pressure
  4. washThe resulting solid was washed with hexane

Sources & evidence

ORD record
ord-2415027a17ad4c6ca14985b8e2120518
Source dataset
uspto-grants-2011_08
Patent number
US08003699B2

Reaction notes

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