Thionyl Chloride → 4-Methylthiophene-2-carbonyl chloride

HRID 971383

Reaction equation

HRID 971383 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:7]([OH:9])=O)[S:5][CH:6]=1.S(Cl)([Cl:12])=O>>[CH3:1][C:2]1[CH:3]=[C:4]([C:7]([Cl:12])=[O:9])[S:5][CH:6]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 27945844-Methylthiophene-2-carboxylic acid

Product 1

HCID 27955254-Methylthiophene-2-carbonyl chloride

Procedure

220 cc of thionyl chloride were progressively added to 50 gm of 4-methyl-thiophene-2-carboxylic acid [prepared by process in Beil, Vol. 18, p. 294] and the mixture was heated to reflux for 1 hour. Excess thionyl chloride was evaporated off under reduced pressure and the residue was distilled under reduced pressure to obtain 51 gm of 4-methyl-thiophene-2-carboxylic acid chloride boiling at 112°-114° C. at 18 mm Hg. which was used as is for the next step. The light yellow liquid was soluble in ether.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customExcess thionyl chloride was evaporated off under reduced pressure
  4. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-c493992beac446d09e5a65cf124daa83
Source dataset
uspto-grants-1979_07
Patent number
US04159986

Linked notes

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