Hydrochloric Acid → HCID 20558300, compound

HRID 1155558Notes

Reaction equation

HRID 1155558 reaction equation
[CH2:1]([CH:3]([CH2:7][CH2:8][CH2:9][CH3:10])[C:4](O)=[O:5])[CH3:2].S(Cl)(Cl)=O.ClN1C(=O)CCC1=O.[ClH:23].[Cl:24]Cl>>[Cl:23][C:3]([CH2:1][CH3:2])([CH2:7][CH2:8][CH2:9][CH3:10])[C:4]([Cl:24])=[O:5]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 86972-Ethylhexanoic AcidHCID 24386Thionyl Chloride2×HCID 24526ChlorineHCID 31398Chlorosuccinimide

Product 1

HCID 20558300HCID 20558300, compoundYield 17.6%

Procedure

To 100 gm of 2-ethylhexanoic acid (0.693 moles) was added 247.5 g of thionyl chloride (2.080 moles) over 30 min. The solution was then heated at 70° for 2 hours. To the cooled solution was added 185.2 gm of N-chloro succinimide (1.387 moles), 165.0 g of thionyl chloride (1.387 moles) and 2.0 ml of concentrated HCl. The mixture was heated at 80° for 2 hours, after which time there was no more apparent Cl2 gas being given off. The mixture was cooled and filtered. The filtrate was distilled at atmospheric pressure to remove the SOCl2 and then distilled to give a major fraction at 95°-105° C. (20 mm) weighing 28.00 gm. Purity was determined by GLC analysis. Purity (area %) was 85.7%; yield was 17.6%. NMR showed no detectable extra chlorination.

Workup

  1. temperatureThe solution was then heated at 70° for 2 hours
  2. temperatureThe mixture was heated at 80° for 2 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. distillationThe filtrate was distilled at atmospheric pressure
  6. customto remove the SOCl2
  7. distillationdistilled
  8. customto give a major fraction at 95°-105° C. (20 mm)

Sources & evidence

ORD record
ord-97f1118481ed4151a8f2dd439bff47b4
Source dataset
uspto-grants-1981_11
Patent number
US04302569

Reaction notes

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