Thionyl Chloride → 3-Methoxy-4-(2-propynyloxy)benzoyl chloride
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
Product 1
Reagents, catalysts & solvents 2
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 mixture obtained was heated under reflux for 3 hours. Then, the reaction mixture was concentrated. The solid obtained was washed with hexane to obtain 11.0 g of 4-(2-propynyloxy)-3-methoxybenzoyl chloride represented by the formula.
Workup
- customthe mixture obtained
- temperaturewas heated
- temperatureunder reflux for 3 hours
- concentrationThen, the reaction mixture was concentrated
- customThe solid obtained
- washwas washed with hexane
Sources & evidence
- ORD record
- ord-c4844b0198954552a6ae17f7c6d001e8
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07902400B2
Reaction notes
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