Thionyl Chloride → 2-Methyl-3-thiophenecarboxylate chloride

Reaction equation

[CH3:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([OH:9])=[O:8].S(Cl)([Cl:12])=O>>[Cl-:12].[CH3:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O-:9])=[O:8]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 46254092-Methylthiophene-3-carboxylic acid

Product 1

HCID 225034702-Methyl-3-thiophenecarboxylate chloride

Procedure

2-Methyl-3-thiophenecarboxylic acid (54 g) was reacted with thionyl chloride (100 ml) at 60° C. for 1.5 hr. The reaction solution was evaporated, and to the resulting residue was added THF (100 mlx2), and then excess thionyl chloride was removed, to give 60.5 g of the title compound.

Workup

customThe reaction solution was evaporated
additionto the resulting residue was added THF (100 mlx2)
customexcess thionyl chloride was removed

Sources & evidence

ORD record: ord-bcd7b10d379a498a85e84b9d085992b6
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06790844B2

Reaction notes

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