Thionyl Chloride → 3,5-Dimethoxy-4-(2-propynyloxy)benzoyl chloride

HRID 1675568Notes

Reaction equation

HRID 1675568 reaction equation
[CH2:1]([O:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[O:16][CH3:17])[C:2]#[CH:3].S(Cl)([Cl:20])=O>CN(C=O)C.C1(C)C=CC=CC=1>[CH2:1]([O:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:8]([C:9]([Cl:20])=[O:10])=[CH:7][C:6]=1[O:16][CH3:17])[C:2]#[CH:3]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 131214813,5-Dimethoxy-4-[(prop-2-yn-1-yl)oxy]benzoic acid

Product 1

HCID 574456693,5-Dimethoxy-4-(2-propynyloxy)benzoyl chlorideYield 85.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

To 100 ml of toluene were added 13.0 g of 4-(2-propynyloxy)-3,5-dimethoxybenzoic acid, 9.5 g of thionyl chloride and 50 mg of DMF, and the resulting mixture was heated under 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 12.0 g of 4-(2-propynyloxy)-3,5-dimethoxybenzoyl chloride was obtained.

Workup

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

Sources & evidence

ORD record
ord-e1fef0b99fa8410aaef96e73c2a56890
Source dataset
uspto-grants-2011_08
Patent number
US08003699B2

Reaction notes

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