Potassium Hydroxide → 22-(Nonafluorobutyl)-1-docosanol

HRID 336067Notes

Reaction equation

HRID 336067 reaction equation
C(CCCCCCCCCCCCCCCCCO)(C(C(C(F)(F)F)(F)F)(F)F)(F)F.[C:32]([CH2:45][CH:46]([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][OH:68])I)([C:35]([C:38]([C:41]([F:44])([F:43])[F:42])([F:40])[F:39])([F:37])[F:36])([F:34])[F:33].[OH-].[K+].[H][H]>C(O)(=O)C.[Zn]>[C:32]([CH2:45][CH2:46][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][OH:68])([C:35]([C:38]([C:41]([F:42])([F:43])[F:44])([F:40])[F:39])([F:37])[F:36])([F:34])[F:33]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 87720095HCID 87720095, compoundHCID 131732012HCID 131732012, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 2263049722-(Nonafluorobutyl)-1-docosanol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

In a similar manner to the synthesis of C4F9(CH2)17OH above, C4F9CH2CHI(CH2)20OH was treated with zinc in glacial acetic acid to afford a mixture of the reduction product alcohols and acetates as well as their corresponding olefins. The mixture was treated essentially as described above with potassium hydroxide to hydrolyze the acetate esters and finally treated with hydrogen to remove the olefinic impurities and recrystallized from hexane. Approximately 16.8 g of white solids C4F9(CH2)22OH was obtained from this process with 98% purity as confirmed by GC/MS.

Workup

  1. customto afford
  2. additionThe mixture was treated essentially
  3. customto remove the olefinic impurities
  4. customrecrystallized from hexane

Sources & evidence

ORD record
ord-3f51436435e24614a3f5a9eac69d7b91
Source dataset
uspto-grants-2014_11
Patent number
US08889230B2

Reaction notes

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