Sodium chlorodifluoroacetate → HCID 13108921, compound

HRID 1277427Notes

Reaction equation

HRID 1277427 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](=[CH2:17])[C:12]([O:14]CC)=[O:13].Cl[C:19]([F:24])([F:23])C([O-])=O.[Na+]>S1(CCCC1)(=O)=O>[F:23][C:19]1([F:24])[CH2:17][C:11]1([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 2734985Sodium chlorodifluoroacetateHCID 13108918HCID 13108918, compound

Product 1

HCID 13108921HCID 13108921, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
160 °C

Procedure

Ethyl 2-(2-naphthyl)-acrylate (4.28 g) was dissolved in sulfolane 20 ml. Sodium chlorodifluoroacetate (9.1 g) was added in portions to the solution, heated to 160° C., over 35 minutes. The reaction mixture was cooled, quenched into ice water, then extracted with ether. The ether layer was washed several times with water and after separation dried over anhydrous sodium sulphate. After evaporation of the ether, the residual dark oil was chromatographed on silica gel using petroleum ether (b.p. 40°-60°)/methylene chloride mixture as eluent. The major fraction (4.05 g) was distilled under vacuum to yield the product as a yellow oil (3.92 g; 71%). The ester was identified from i.r. and p.m.r. spectra and hydrolysed by refluxing in 1 N sodium hydroxide/ethanol solution. On acidification and extraction the solid acid was recrystallised from petroleum ether/methylene chloride to yield the acid as a white solid, m.p. 190°-2°.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched into ice water
  3. extractionextracted with ether
  4. washThe ether layer was washed several times with water
  5. customafter separation
  6. dry with materialdried over anhydrous sodium sulphate
  7. customAfter evaporation of the ether
  8. customthe residual dark oil was chromatographed on silica gel
  9. distillationThe major fraction (4.05 g) was distilled under vacuum

Sources & evidence

ORD record
ord-36136f86134c49aa8c4d62e686da52dc
Source dataset
uspto-grants-1981_07
Patent number
US04277490

Reaction notes

Loading…