Sulfuric Acid → C4F9CH2CF2CH2CH2OH

HRID 1452452Notes

Reaction equation

HRID 1452452 reaction equation
[C:1]([CH2:14][C:15]([CH2:18][CH2:19]I)([F:17])[F:16])([C:4]([C:7]([C:10]([F:13])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2].S(=O)(=O)(O)[OH:22]>>[F:16][C:15]([F:17])([CH2:14][C:1]([F:3])([F:2])[C:4]([F:6])([F:5])[C:7]([F:9])([F:8])[C:10]([F:13])([F:12])[F:11])[CH2:18][CH2:19][OH:22]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 858357771,1,1,2,2,3,3,4,4,6,6-Undecafluoro-8-iodooctane

Product 1

HCID 57526216C4F9CH2CF2CH2CH2OH

Conditions

Temperature
60 °C

Procedure

Fuming sulfuric acid (70 mL) was added slowly to 50 g of C4F9CH2CF2CH2CH2I and mixture stirred at 60° C. for 1.5 h. The reaction was quenched with ice-cold 1.5 wt % Na2SO3 aqueous solution and heated at 95° C. for 0.5 h. The bottom layer was separated and washed with 10 wt % aqueous sodium acetate, and distilled to provide 3,3,5,5,6,6,7,7,8,8,8-undecafluorooctan-1-ol (compound A6): bp 54-57° C. at 2 mmHg.

Workup

  1. customThe reaction was quenched with ice-cold 1.5 wt % Na2SO3 aqueous solution
  2. temperatureheated at 95° C. for 0.5 h
  3. customThe bottom layer was separated
  4. washwashed with 10 wt % aqueous sodium acetate
  5. distillationdistilled

Sources & evidence

ORD record
ord-14478f44eba14576837999a2cd70d24e
Source dataset
uspto-grants-2009_01
Patent number
US07473658B2

Reaction notes

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