1-Fluorododecane → 1-Dodecanol

HRID 420172Notes

Reaction equation

HRID 420172 reaction equation
[C:1](=[O:4])([O-])O.[Na+].F[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]C>>[CH2:1]([OH:4])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH3:7]

Participants

3

Reactant 2

HCID 95481-FluorododecaneHCID 516892Sodium Bicarbonate

Product 1

HCID 81931-Dodecanol

Procedure

93 mg (0.5 mmol) of dodecanol purified by distillation, 0.39 g (0.6 mmol, 1.2 equivalents) of N,N-diethyl-α,α-difluoro-[4-(1H,1H,2H,2H-perfluorodecyl)benzyl]amine (compound c) produced in Example 1, and 0.5 ml of heptane were put into a container formed of PFA (tetrafluoroethylene/perfluoroalkyl vinyl ether copolymer), and reacted in a nitrogen atmosphere at 100° C. for 3 hours. After the reaction, an aqueous saturated sodium hydrogencarbonate solution was added thereto for neutralization, and then the product was extracted out with dichloromethane. The solvent was evaporated away, followed by purification through silica gel column chromatography (solvent: dichloromethane/diethyl ether mixed solvent) to give a product. The main product was 1-fluorododecane, and its yield was 86%.

Workup

  1. customreacted in a nitrogen atmosphere at 100° C. for 3 hours
  2. customAfter the reaction
  3. extractionfor neutralization, and then the product was extracted out with dichloromethane
  4. customThe solvent was evaporated away
  5. customfollowed by purification through silica gel column chromatography (solvent: dichloromethane/diethyl ether mixed solvent)
  6. customto give a product

Sources & evidence

ORD record
ord-1db4ae80b74840d384cdd9d0237775af
Source dataset
uspto-grants-2012_01
Patent number
US08093429B2

Reaction notes

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