Sulfuryl chloride → Methyl 3-hydroxy-5-methylthiophene-2-carboxylate

HRID 1732943Notes

Reaction equation

HRID 1732943 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH:9]([OH:10])[CH:8]=[C:7]([CH3:11])[S:6]1)=[O:4].S(Cl)(Cl)(=O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH3:11])=[CH:8][C:9]=1[OH:10])=[O:4]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 537769093-Hydroxy-5-methyldihydrothiophene-2-carboxylic acid methyl ester

Product 1

HCID 587860Methyl 3-hydroxy-5-methylthiophene-2-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

17.4 Parts of 3-hydroxy-5-methyldihydrothiophene-2-carboxylic acid methyl ester are dissolved in 100 parts by volume of methylene chloride. 14.9 parts of sulfuryl chloride in 20 parts by volume of methylene chloride are added in the course of 30 minutes at 10° C., whilst passing nitrogen into the mixture. The mixture is then distilled. 12.9 parts (75% of theory) of 3-hydroxy-5-methylthiophene-2-carboxylic acid methyl ester of boiling point 67°-70° C./0.3 mbar are obtained.

Workup

  1. distillationThe mixture is then distilled

Sources & evidence

ORD record
ord-49e6e8169b1c4d8091332137711260ac
Source dataset
uspto-grants-1980_12
Patent number
US04239897

Reaction notes

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