Methanol → Methyl perfluoroheptanoate

HRID 1810720Notes

Reaction equation

HRID 1810720 reaction equation
[F:1][C:2]([F:22])([C:6]([F:21])([F:20])[C:7]([F:19])([F:18])[C:8]([F:17])([F:16])[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])[C:3]([OH:5])=[O:4].[CH3:23]O.S(=O)(=O)(O)O>O>[F:1][C:2]([F:22])([C:6]([F:20])([F:21])[C:7]([F:18])([F:19])[C:8]([F:17])([F:16])[C:9]([F:14])([F:15])[C:10]([F:13])([F:12])[F:11])[C:3]([O:5][CH3:23])=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 67818Perfluoroheptanoic acid

Product 1

HCID 526471Methyl perfluoroheptanoateYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 2-1, four-necked, round-bottomed flask equipped with stirrer, addition funnel, thermometer and reflux condenser, is charged with 728 g (2 mol) of dried perfluoroheptanoic acid, 160 g (5 mol) of methanol. The mixture is stirred and added dropwise 50 ml concentrated sulfuric acid and then heated to reflux for 4 hr. At the end of the reflux period the mixture is cooled to room temperature and poured into 2 l cold water. After separation of the phases, the lower organic phase is washed with water till pH neutral and dried over CaCl2. Distillation of the crude gives 658 g (87%) of methyl perfluoroheptanoate, bp 139° C.

Workup

  1. customA 2-1, four-necked, round-bottomed flask equipped with stirrer, addition funnel
  2. temperaturethermometer and reflux condenser
  3. temperatureheated
  4. temperatureto reflux for 4 hr
  5. customAfter separation of the phases
  6. washthe lower organic phase is washed with water till pH neutral and
  7. dry with materialdried over CaCl2
  8. distillationDistillation of the crude

Sources & evidence

ORD record
ord-14f9b002b3774716abdc7366685ebfc1
Source dataset
uspto-grants-2013_01
Patent number
US08362167B2

Reaction notes

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