Sulfuric Acid → Perfluoro-2-[3-(methoxy)propoxy]acetic acid

HRID 2407644Notes

Reaction equation

HRID 2407644 reaction equation
[K+].[Br-].[F:3][C:4]([F:22])([O:7][C:8]([F:21])([F:20])[C:9]([F:19])([F:18])[C:10]([F:17])([F:16])[O:11][C:12]([F:15])([F:14])[F:13])[CH2:5][OH:6].[O-]Cl.[Na+].S(=O)(=O)(O)[OH:27]>CC1(C)N([O])C(C)(C)CCC1.O.CC#N>[F:3][C:4]([F:22])([O:7][C:8]([F:20])([F:21])[C:9]([F:18])([F:19])[C:10]([F:16])([F:17])[O:11][C:12]([F:13])([F:14])[F:15])[C:5]([OH:27])=[O:6]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 253877Potassium BromideHCID 23665760Sodium HypochloriteHCID 66573360HCID 66573360, compound

Product 1

HCID 52915300Perfluoro-2-[3-(methoxy)propoxy]acetic acidYield 87%

Reagents, catalysts & solvents 3

HCID 2724126TempoCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

5.5 mL water, 16 ml MeCN, 0.32 g KBr, TEMPO (0.11 g), and 8 g of 2,2-difluoro-2-(1,1,2,2,3,3-hexafluoro-3-trifluoromethoxy-propoxy)-ethanol are placed in a 100 ml glass flask equipped with a dropping funnel and stirrer. 43 mL of 15% (wt) aq. NaOCl buffered to pH 8-9 were added via the dropping funnel in 3 portions over two days while stirring at room temperature. Concentrated sulphuric acid and water were added to bring the pH to about 1 to 2. The reaction mixture was extracted three times by diethyl ether and the combined ether phases were dried over magnesium sulphate. The solvent was evaporated to give colorless liquid, which was distilled using a water pump (15 mmHg, 70° C.) to give 7.25 g of the acid. Yield: 87%. 1H NMR (CDCl3): 9.39 (s, 1H); 19F NMR (CDCl3): −56.28 (t, J=8.7 Hz, 3F); −79.19 (t, J=11.9 Hz, 2F); −84.58 (m, 2F); −86.86 (m, 2F); −130.45 (m, 2F).

Workup

  1. customequipped with a dropping funnel and stirrer
  2. additionwere added via the dropping funnel in 3 portions over two days
  3. extractionThe reaction mixture was extracted three times by diethyl ether
  4. dry with materialthe combined ether phases were dried over magnesium sulphate
  5. customThe solvent was evaporated
  6. customto give colorless liquid, which
  7. distillationwas distilled
  8. customa water pump (15 mmHg, 70° C.)

Sources & evidence

ORD record
ord-e557594e90a744c581feb4f7eea45bde
Source dataset
uspto-grants-2014_08
Patent number
US08809580B2

Reaction notes

Loading…