Hydrochloric Acid → 1,1,1,2,2,3,3,4,4,5,5,6,6,11,11,12,12,13,13,14,14,15,15,16,16,16-Hexacosafluorohexadecane

HRID 1385311Notes

Reaction equation

HRID 1385311 reaction equation
[Mg].[C:2]([CH2:21][CH2:22]I)([C:5]([C:8]([C:11]([C:14]([C:17]([F:20])([F:19])[F:18])([F:16])[F:15])([F:13])[F:12])([F:10])[F:9])([F:7])[F:6])([F:4])[F:3].Cl.C(Cl)(Cl)Cl>C(OCCC)CC.CI>[C:2]([CH2:21][CH2:22][CH2:22][CH2:21][C:2]([C:5]([C:8]([C:11]([C:14]([C:17]([F:18])([F:19])[F:20])([F:15])[F:16])([F:12])[F:13])([F:10])[F:9])([F:7])[F:6])([F:4])[F:3])([C:5]([C:8]([C:11]([C:14]([C:17]([F:20])([F:19])[F:18])([F:16])[F:15])([F:13])[F:12])([F:10])[F:9])([F:7])[F:6])([F:4])[F:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 748881,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctaneHCID 5462224Magnesium2×

Product 1

HCID 125960311,1,1,2,2,3,3,4,4,5,5,6,6,11,11,12,12,13,13,14,14,15,15,16,16,16-HexacosafluorohexadecaneYield 63.4%

Reagents, catalysts & solvents 2

HCID 6328Methyl iodideCatalystHCID 8114Propyl etherSolvent2×

Procedure

In accordance with K. von Werner, DE 39 25 525 A1 (1989), in a four-necked flask of 250 cm3 capacity, which is equipped with a dropping funnel (with bypass for pressure equalization), vane stirrer, thermometer and reflux condenser with superimposed check valve, 1.82 g (0.075 mol) magnesium chips are placed under argon in 10 cm3 of anhydrous di-n-propyl ether and activated with a few drops of methyl iodide with gentle heating. The temperature is raised to 80° C. while a mixture of 23.7 g (0.05 mol) of C6F13CH2CH2I and 60 cm3 of anhydrous di-n-propyl ether is added drop by drop within one hour with vigorous stirring. Then the mixture is stirred with refluxing for 9 hours and then cooled to 10° C., hydrolyzed with 100 cm3 of 5 wt.-% aqueous hydrochloric acid until the excess magnesium has dissolved. Then the ether phase is separated and concentrated with a rotary evaporator. The oily residue thus obtained is treated with 30 cm3 of chloroform and let stand for 1 hour at 0° C. The solid product precipitated from the mixture is suction filtered and dried in the desiccator. 11.0 g of C6F13(CH2)4C6F13 is obtained as nearly colorless crystals which have a melting point of 48° C. The yield is 63.2% of the theoretical.

Workup

  1. temperaturethermometer and reflux condenser with superimposed check valve
  2. additionis added drop by drop within one hour with vigorous stirring
  3. temperaturewith refluxing for 9 hours
  4. dissolutionhas dissolved
  5. customThen the ether phase is separated
  6. concentrationconcentrated with a rotary evaporator
  7. customThe oily residue thus obtained
  8. customThe solid product precipitated from the mixture
  9. filtrationfiltered
  10. customdried in the desiccator

Sources & evidence

ORD record
ord-15d78c4e21444d34967e53187c51c661
Source dataset
uspto-grants-2001_07
Patent number
US06262126B1

Reaction notes

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