5:1 Fluorotelomer alcohol → HCID 53902667, compound

HRID 1740683Notes

Reaction equation

HRID 1740683 reaction equation
[CH2:1]1[O:3][C@@H:2]1[CH2:4][OH:5].[F:6][C:7]([F:23])([C:10]([F:22])([F:21])[C:11]([F:20])([F:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])[CH2:8][OH:9]>CCN(C(C)C)C(C)C>[OH:3][C@H:2]([CH2:1][O:9][CH2:8][C:7]([F:23])([F:6])[C:10]([F:21])([F:22])[C:11]([F:19])([F:20])[C:12]([F:17])([F:18])[C:13]([F:16])([F:15])[F:14])[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 27824055:1 Fluorotelomer alcoholHCID 5460455(+)-Glycidol

Product 1

HCID 53902667HCID 53902667, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineCatalyst

Procedure

(S)-2-hydroxy-3-(2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyloxy)-propanol was prepared by the following modification of a procedure described in U.S. Pat. No. 3,470,258 (Teroso et al.). (R)-glycidol (5.0 g, 67.5 mmol) was added dropwise to a 120° C. solution of 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexanol (30 g, 101 mmol) and N,N'-diisopropylethylamine (0.47 ml, 2.7 mmol). The resulting mixture was then stirred for one hour. The resulting product was distilled (79-81° C. at 0.4 mm Hg) from the mixture to give 14.7 g of (S)-2-hydroxy-3-(2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyloxy)-1-propanol as a clear liquid. (R)-2-fluoro-3-(2,2,3,3,4,4,5,5,6,6,6-undecafluorohexane-1-p-toluenesulfonate was then prepared using essentially the procedure described in Example 1.

Workup

  1. custom(S)-2-hydroxy-3-(2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyloxy)-propanol was prepared by the following modification of a procedure
  2. distillationThe resulting product was distilled (79-81° C. at 0.4 mm Hg) from the mixture

Sources & evidence

ORD record
ord-0f6f22b7dbd44c3697d0d2d8798c11b9
Source dataset
uspto-grants-1999_10
Patent number
US05972241

Reaction notes

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