Hydrochloric Acid → HCID 22997623, compound

HRID 1166207Notes

Reaction equation

HRID 1166207 reaction equation
C([O:3][C:4](=[O:14])[C:5]([C:7]1[S:8][C:9]([Cl:13])=[C:10]([Cl:12])[CH:11]=1)=[O:6])C.Cl.C(Cl)Cl>CC(C)=O.O>[Cl:12][C:10]1[CH:11]=[C:7]([C:5](=[O:6])[C:4]([OH:14])=[O:3])[S:8][C:9]=1[Cl:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 66934444HCID 66934444, compound

Product 1

HCID 22997623HCID 22997623, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A solution of (4,5-dichlorothiophen-2-yl)-oxo-acetic acid ethyl ester (2.53 g, 10.0 mmol) in acetone (15 ml), water (5 ml), and conc. HCl (20 ml) was stirred under reflux for 2 hr. The reaction mixture was then allowed to cool to ambient temperature and was poured into CH2Cl2 and water. The organic layer was dried over Na2SO4 and concentrated under vacuum. Crystallization of the residue from dichloromethane provided pure (4,5-dichlorothiophen-2-yl)-oxo-acetic acid as a yellow solid (557 mg, 25%). MS (M−H)−: 222.78; 1H NMR (300 MHz, DMSO-d6) δ8.06 (s).

Workup

  1. temperatureunder reflux for 2 hr
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customCrystallization of the residue from dichloromethane provided pure (4,5-dichlorothiophen-2-yl)-oxo-acetic acid as a yellow solid (557 mg, 25%)

Sources & evidence

ORD record
ord-177942be89a64603ab17e53802a0ac63
Source dataset
uspto-grants-2003_09
Patent number
US06613786B2

Reaction notes

Loading…