1-Nonanol, 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodo- → 4,4,5,5,6,6,7,7,8,8,9,9,9-Tridecafluorononan-1-ol

HRID 393411Notes

Reaction equation

HRID 393411 reaction equation
I[CH:2]([CH2:5][C:6]([F:24])([F:23])[C:7]([F:22])([F:21])[C:8]([F:20])([F:19])[C:9]([F:18])([F:17])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[CH2:3][OH:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:23][C:6]([F:24])([C:7]([F:21])([F:22])[C:8]([F:19])([F:20])[C:9]([F:17])([F:18])[C:10]([F:15])([F:16])[C:11]([F:12])([F:14])[F:13])[CH2:5][CH2:2][CH2:3][OH:4]

Participants

4

Reactant 2

HCID 1700641-Nonanol, 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodo-HCID 21226445Aluminium lithium hydride

Product 1

HCID 27761814,4,5,5,6,6,7,7,8,8,9,9,9-Tridecafluorononan-1-olYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-iodo-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononan-1-ol 19 (15 g, 29.8 mmol) was slowly added to a solution of lithium aluminum hydride (1.14 g, 30.1 mmol) in THF (60 mL). After stirring at room temperature overnight, the reaction mixture was quenched with ethylacetate (5 mL). Water (150 mL) was added to the mixture and extracted with ether (3×75 mL). Ether layers were combined, washed with water and brine solution. The ether layer was then concentrated and distilled to get 20 (8.66 g, 77%) bp 90-92° C. at aspirator pressure; 1H NMR (CDCl3) δ3.75 (t, J=6.1 Hz, 2H), δ2.31-2.13 (mn, 2H), δ1.92-1.83 (mn, 2H)

Workup

  1. customthe reaction mixture was quenched with ethylacetate (5 mL)
  2. additionWater (150 mL) was added to the mixture
  3. extractionextracted with ether (3×75 mL)
  4. washwashed with water and brine solution
  5. concentrationThe ether layer was then concentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-cfbf51204fe8413590f69591030d92f8
Source dataset
uspto-grants-2004_10
Patent number
US06806357B1

Reaction notes

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