Acetic Acid → HCID 86650338, compound

HRID 1799809Notes

Reaction equation

HRID 1799809 reaction equation
C(O)(=O)C.[C:5]([C:7]([C:26]#[N:27])([CH2:20][CH2:21][C:22]([F:25])([F:24])[F:23])[CH2:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:13]2(OCC[O:14]2)[CH2:12][CH2:11]1)#[N:6]>O>[C:5]([C:7]([C:26]#[N:27])([CH2:20][CH2:21][C:22]([F:25])([F:24])[F:23])[CH2:8][CH2:9][CH:10]1[CH2:11][CH2:12][C:13](=[O:14])[CH2:18][CH2:19]1)#[N:6]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 86650339HCID 86650339, compound

Product 1

HCID 86650338HCID 86650338, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To 20 mL of a 50% aqueous acetic acid solution, 1.85 g of 8-(3,3-dicyano-6,6,6-trifluorohexyl)-1,4-dioxaspiro[4.5]decane was added, followed by stirring at 50° C. for 8 hours under a nitrogen atmosphere. To the reaction mixture was added 100 mL of water, followed by extraction twice with 100 mL of ethyl acetate. The combined organic layer was washed sequentially with 100 mL of a saturated aqueous sodium hydrogen carbonate solution and 100 mL of a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.37 g of 4-(3,3-dicyano-6,6,6-trifluorohexyl)cyclohexanone represented by the following formula:

Workup

  1. extractionfollowed by extraction twice with 100 mL of ethyl acetate
  2. washThe combined organic layer was washed sequentially with 100 mL of a saturated aqueous sodium hydrogen carbonate solution and 100 mL of a saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e951506a25f6443da2c49b7d00381e44
Source dataset
uspto-grants-2013_01
Patent number
US08344163B2

Reaction notes

Loading…