Water → HCID 10751251, compound

HRID 749407Notes

Reaction equation

HRID 749407 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[N:8].[CH2:9]([OH:17])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.C(OCC)(=O)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[OH-].[Na+]>[CH2:9]([O:17][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[N:8])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 962WaterHCID 60542-PhenylethanolHCID 8857Ethyl AcetateHCID 810936-Bromohexanenitrile

Product 1

HCID 10751251HCID 10751251, compoundYield 104.3%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
65 °C

Procedure

6-Bromohexanenitrile (3.0 mL, 23 mmol) and tetrabutylammonium bromide (350 mg, 1.1 mmol) were dissolved in tetrahydrofuran (5 mL) and 50% aqueous sodium hydroxide (15 mL). Phenethyl alcohol (3.0 mL, 25 mmol) was added resulting in a precipitate. The mixture was heated to 65° C. whereupon the solid dissolved. The mixture was stirred at 65° C. for four hours then cooled to room temperature and left for 11 days. Water, hexanes and ethyl acetate were added and the mixture partitioned. The organics were washed with water, saturated sodium chloride, dried over sodium sulfate and evaporated to dryness to give the title intermediate (5.3 g, 24 mmol) which was used without further purification.

Workup

  1. customresulting in a precipitate
  2. dissolutiondissolved
  3. temperaturethen cooled to room temperature
  4. waitleft for 11 days
  5. customthe mixture partitioned
  6. washThe organics were washed with water, saturated sodium chloride
  7. dry with materialdried over sodium sulfate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-99e8330e58d34b3abdcb377786317613
Source dataset
uspto-grants-2008_07
Patent number
US07402673B2

Reaction notes

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