Phosphoric Acid → 1-(5-Chloro-4-methyl-2-thienyl)ethanone

HRID 280563Notes

Reaction equation

HRID 280563 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH3:7].[C:8](OC(=O)C)(=[O:10])[CH3:9].P(=O)(O)(O)O>O>[Cl:1][C:2]1[S:3][C:4]([C:8]([CH3:9])=[O:10])=[CH:5][C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 7918Acetic AnhydrideHCID 843652-Chloro-3-methylthiophene

Product 1

HCID 133762171-(5-Chloro-4-methyl-2-thienyl)ethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 20 g (0,15 mol) of 2-chloro-3-methylthiophene and 18,6 g (0,18 mol) of acetic acid anhydride were heated to 70° C. and 1,8 ml of orthophosphoric acid were dropped thereto such that the reaction temperature remained below 75° C. Then it was stirred 3 hours at 100° C., 50 ml of H2O were added, the organic phase was extracted twice with 10 ml of saturated NaHCO3 -solution, dried over Na2SO4 and fractionated distilled in vacuo. Yield 15,8 g (60%), b.p. 85°-88° C./4 mbar.

Workup

  1. customremained below 75° C
  2. extractionthe organic phase was extracted twice with 10 ml of saturated NaHCO3 -solution
  3. dry with materialdried over Na2SO4
  4. distillationfractionated distilled in vacuo

Sources & evidence

ORD record
ord-904695b7ffd64348839c5c2ca08b8c51
Source dataset
uspto-grants-1986_05
Patent number
US04590203

Reaction notes

Loading…